Talk:Paclitaxel total synthesis

Paclitaxel or taxol

Hi User:Alvis, I do not doubt your sincere intentions when you exchanged taxol with Paclitaxel in the title of this article but if you look at the references all titles state only Taxol trade name or not. What can I do to discourage you from changing the other titles in this cluster or even revert to the original title. The references cited should dictate the naming conventions. Thanks in advance for your reply V8rik 12:20, 6 October 2007 (UTC)[reply]

Thanks for taking this up on the Talk page instead of just reverting. From what I've read at Wikipedia:WikiProject Pharmacology/Style guide, the International Nonproprietary Name is preferred to any commercial names for compounds. With a redirect for Taxol total synthesis, I don't think there'll be a problem. Alvis 05:38, 8 October 2007 (UTC)[reply]

This is not a pharmacology article, this is an organic synthesis article and should use the name that is overwhelmingly used in the organic synthesis literature. I suggest reverting back to Taxol. --Itub 09:35, 9 October 2007 (UTC)[reply]

Taxol total synthesis is a much more familiar term than paclitaxel total synthesis. I think the name most commonly used in papers should be preferred. --Rifleman 82 07:43, 11 October 2007 (UTC)[reply]

Paclitaxel should be used in the Pharmacology article and for the total synthesis we should go back to the name everybody knows Taxol-Stone 07:59, 11 October 2007 (UTC)[reply]

I was hoping that WP, being what it is and stands for, would lean towards non-commercial, globally-preferred scientific names for molecules and their related articles, but consensus is consensus. Alvis 08:12, 11 October 2007 (UTC)[reply]

We are not here to prescribe non-commercial names based on idealistic principles, but to reflect the way things are called in the real world. --Itub 08:47, 11 October 2007 (UTC)[reply]

Two things: First Taxol total synthesis is more part of WikiProject Chemistry than Pharmacology an therfore the Wikipedia:WikiProject Pharmacology/Style guide is not valide fotr the title. Second the style guide is only a guide and not a law, if it it is not good in a certain case you can do otherwise.--Stone 11:58, 11 October 2007 (UTC)[reply]

Third search yields thousand hits for taxol total synthesis and below 10 for Paclitaxel total synthesis which makes it clear what the name should be.--Stone 12:02, 11 October 2007 (UTC)[reply]

If this falls under WikiProject Chemistry, then isn't the INN recommendation at Wikipedia:Naming conventions (chemistry) the end of this discussion? Alvis 08:07, 19 October 2007 (UTC)[reply]

No, because of the "General rule" and the "Exceptions" sections. --Itub 08:10, 19 October 2007 (UTC)[reply]

Paclitaxel/Taxol synthesis RFC

Fixed RFCxxx template, set section param to section heading. DMcMPO11AAUK/Talk/Contribs 03:44, 26 October 2007 (UTC)[reply]

Do WP pharmacology guidelines for INNs apply to organic synthesis articles? —Preceding unsigned comment added by Alvis (talk • contribs) 07:40, 11 October 2007 (UTC)[reply]

I would say that the INN should be used, although I'm sympathetic to Itub's point that organic chemists usually just refer to the compound as Taxol. Wikipedia:Naming conventions (chemistry) recommends INNs (where these exist) for articles about chemicals, and it seems a bit illogical to use a different name for the article about the total synthesis. The only exception that I know of is Asprin (whose INN is acetylsalicylic acid), and I think we would be opening Pandora's box to promote any more (see constant squabbles at paracetamol, for example). Physchim62 (talk) 11:08, 11 October 2007 (UTC)[reply]

The acetaminophen is a good example, but I stil do not like it, the point is that all mentionings on the page should be consistent and than all Taxols should be converted to Paclitaxel. --Stone 14:35, 11 October 2007 (UTC)[reply]

Subsequentially all other total synthesis articles of taxol have to be renamed to and the renaming to Nicolaou Paclitaxel total synthesis I would revert without hesitation.--Stone 14:49, 11 October 2007 (UTC)[reply]

Per Physchim62's comment - I too fear that in the long run, since commercial rights fade, it's in WP's best interest to promote a universal nomenclature. I realize that the other published synths use "taxol", but we should keep in mind that it's in any chemist's best interest to have his/her work readily accessible when being searched for by peers that may only be familiar with as-of-then popular terms. If not enough users agree with this, than this article should be reverted, and I'll take my concerns up elsewhere if I feel that a formal WP policy needs to be established in the best interest of long-term naming. Per Stone, I was about to edit the rest of the synth articles for consistency per INNs, but held back until this could be resolved.Alvis 10:17, 12 October 2007 (UTC)[reply]

Taxol is the trade name from 1939 for something total different, but was granted (1992) long after the Taxol was used for the extract from Taxus for an anti tumar agent. Nature suffered from this dispute and we should stand up against that hijacking of the name. doi:10.1038/373370a0-Stone 16:09, 11 October 2007 (UTC)[reply]

I agree that the INN should be used as well (but that a redirect is also warranted because of the common use). For that matter, I would move Aspirin around too; the existence of a redirect is sufficient to allay any concern about someone searching for a usual name, but given that this is an encyclopedia we should be striving for the proper terminology within the main heading articles. Note Teflon -> Polytetrafluoroethylene (and not, say, Teflon (chemical)). — Coren ^(talk) 03:05, 16 October 2007 (UTC)[reply]
- On the other hand, an encyclopedia should reflect common usage and that's the greatest strength of Wikipedia — being constantly up-to-date. Further, if common usage is not incorrect (e.g. mass spectrometry vs. mass spectroscopy; supernate vs. supernatant), even less reason to change. --Rifleman 82 03:31, 16 October 2007 (UTC)[reply]
  - Which is why a redirect from the common name is both useful and warranted. Usable and instructive! Yeay! If there is a trade name in common use, mention in the article as well is also a good option. "Foo, also known by the trade name bar is a quux that baz..." — Coren ^(talk) 12:41, 16 October 2007 (UTC)[reply]
- But who decides what the "proper terminology" is? IUPAC? ISO? WHO? There are multiple authorities that could be used, and not all of them will give you the same name. Also, even if an authority makes a recommendation, it would be naively idealistic to follow it if very few people follow it in the real world (as happens with some IUPAC recommendations, for example). That said, after conducting a quick search of some of the recent chemistry literature, it does seem like paclitaxel is slowly overtaking taxol in terms of usage. And the ACS Style Guide recommends paclitaxel over taxol. To conclude, I'm less reluctant now to accept paclitaxel as a name, although it is still far from standard in chemistry IMO. --Itub 07:54, 16 October 2007 (UTC)[reply]
  - That's a fair question, but in most fields there is at most one (or two) authority for terminology, and they tend to agree. When there is a dispute, noting it in the article would also make sense: vis. the mess with elements 104-106. — Coren ^(talk) 12:41, 16 October 2007 (UTC)[reply]
    - I also support the use of the INN in this case. Paclitaxel is not an unknown obscure name. I am certain all of the authors of the papers cited that use taxol are aware of the name paclitaxel and are most likely using that terminology today at least occasionally. A redirect along with text indicating alternative names is sufficient. I say the ACS style guide is pretty authoritative. I also agree that *sometimes* naming conventions are completely ignored by the scientific community, in which case we should also make an exception. This is not such a case. Common but not universal (but growing) use plus naming conventions and usage recommendations make paclitaxel the best choice for the name space. A redirect and explanation is needed.--Nick Y. 19:57, 19 October 2007 (UTC)[reply]
      - Nick Y., do you think the current article, mentioning Taxol in parenthesis after Paclitaxel is sufficient, or should we do more to explain that Taxol is the primary commercial name, and Paclitaxel, the preferred international name, is also the name of the article for the molecule itself? Alvis 05:02, 26 October 2007 (UTC)[reply]
        I'm not Nick, but I'd suggest mentioning somewhere (it could be a footnote) that the original publications used the name "taxol", because that was the name in common use at the time. After all, the name wasn't always a trademark! --Itub 07:33, 26 October 2007 (UTC)[reply]
        That's important to be mentioned somewhere, but the article for the molecule already states "... Monroe E. Wall and Mansukh C. Wani isolated it from the bark of the Pacific yew tree, Taxus brevifolia and named it 'taxol'. When it was developed commercially by Bristol-Myers Squibb (BMS) the generic name was changed to 'paclitaxel' and the BMS compound is sold under the trademark 'Taxol®'." It seems more appropriate to include that information like it is now, in the article for the chemical, and leave the synthesis article to the synthesis itself, while maintaining the naming protocols established by the main article. Alvis 06:19, 27 October 2007 (UTC)[reply]
        I'm not saying we should repeat the whole story here, but just add a short note to reduce confusion among readers who find that all of the references call it taxol (I already added it, BTW). Not everyone will have read the main article before this one. --Itub 07:11, 27 October 2007 (UTC)[reply]

Which synthesis was first?

This article and the Holton Taxol total synthesis article say that Holton was first. This should be clarified, however, because it depends on the meaning of "first". ;-) For example, Nicolaou's synthesis was actually published first (Feb. 17 vs Feb 23), while Holton's was submitted for publication first (Dec 21 vs Jan 24). The whole thing has aptly been called a "photofinish" in ChemComm 2003, p. 662.[1] --Itub 13:04, 12 October 2007 (UTC)[reply]

Thanks for the info. I will leave the ref here:

Chem. Commun., 2003, 661 - 664, DOI: 10.1039/b212248k Creating complexity – the beauty and logic of synthesis K. C. Nicolaou

so that I can read the article as soon as possible. By the way if anyone has an online version of the T. Mukaiyama article (ref 5) I would greatly appreciate it (that would finish the project) V8rik 18:57, 12 October 2007 (UTC)[reply]

The point made here is included in the article. V8rik 17:27, 23 October 2007 (UTC)[reply]

I have copies of Mukaiyama's papers around the subject in my hands:

Chem. Lett. 1996, 223. doi:10.1246/cl.1996.223
Chem. Lett. 1997, 1139. doi:10.1246/cl.1997.1139
Chem. Lett. 1998, 1. doi:10.1246/cl.1998.1 (presented in the article as ref)

I can sent you above pdfs via e-mail, but the full paper

Mukaiyama, T. et al. "Asymmetric Total Synthesis of Taxol®." Chem. Eur. J. 1999, 5, 121. doi:10.1002/(SICI)1521-3765(19990104)5:1<121::AID-CHEM121>3.0.CO;2-O

would be better to consult. --Calvero JP 17:42, 27 October 2007 (UTC)[reply]

Thanks, I was unaware of the 1999 publication, that one I should be able to get from my library so that should solve my problem V8rik 20:59, 27 October 2007 (UTC)[reply]

Holton finished in December 93, Nicolaou in January 94 (see [2]), both publishing in February 94, with, as you note, RAH first to submit, and KCN first to see his in print. Tie goes to the runner, and in this case, that perhaps has to be Holton, though both have and are writing their perspectives on this history. Le Prof

If there is not objection

I intend, shortly, to move this article (retitle it as) "Paclitaxel synthesis", reason being to make the correspondence between title and content accurate, with justifications being clearcut, and at least two:

The article contains both "Biosynthesis" and "Semisynthesis" sections, neither of which are "Total synthesis", but both of which are "Synthesis", and these are substantial and valid content segments;
The article does contain information on "Paclitaxel Total Synthesis", but in just one section, essentially co-equal in length and quality alongside the other two sections.

The simplest way to make the title and content accurate is to remove the word "total" from the title, and if not done automatically, to begin repairing links referring just to total synthesis, to the appropriate section of the article.

Will attend to later this week, but will give time for discussion. Le Prof Leprof 7272 (talk) 14:47, 2 June 2014 (UTC)[reply]

Please provide a more detailed rationale I anticipate that you have insight into this and I know almost nothing of this, but in the past, I have been worried because some title changes were proposed which would have resulted in some useful article content being deleted for lack of relevance after a title change. Many articles are in Category:Total synthesis and this proposal could impact all of them. Please respond to past discussion at Talk:Morphine#Merge_morphine_total_synthesis. Again, I acknowledge that there are many discussions saying that these titles are not right, but before there is a title change, I would like to get confirmation that the supporters of a title change are also supporters of preserving the current content of the article (unless it is removed with the usual discussion) and that they sought input from others so that after the title is changed, it goes to something with community support. As someone outside this field, I cannot comment on what title might be appropriate but want to encourage people who can make such comments to help establish a precedent for good style here. Blue Rasberry (talk) 16:00, 2 June 2014 (UTC)[reply]

Hi Leprof 7272, You have requested my presence on this page for comments. The discussion regarding total synthesis pages should they exist at all in Wikipedia has not yet been resolved so for now I will not invest any time in any discussion on a total synthesis page. V8rik (talk) 16:56, 5 June 2014 (UTC)[reply]

@ Blue Rasberry (talk), @V8rik (talk), Per request, holding on any action here until the broader discussions of TS article organization come to their conclusion. Note, for this article, my only desire was to have an accurate correspondence between title and content. From my perspective, this could (in an ideal world) become a standalone article summarizing from bird's eye perspective, the whole series of paclitaxel total syntheses articles that appear, and being maintained as that sort of overarching, perspective article (i.e., keeping the related semisynthesis section, but removing the the biosynthesis section to the main paclitaxel article). Alternatively, it could be renamed as I first suggested, so biosynthesis fits. In suggesting the simpler change, I did not realize I was stumbling onto the minefield of Exercisephys's proposals. On further review, my actual preference here, is for the article to remain with title unchanged, and for the biosynthesis content to be moved. Le Prof Leprof 7272 (talk) 20:03, 5 June 2014 (UTC)[reply]

Why for goodness sake

…does this article not contain any actual Holton citations, as of today—either primary or secondary? Mon Dieu. Le Prof Leprof 7272 (talk) 15:29, 2 June 2014 (UTC)[reply]