Taxadienone

Taxadienone ((+)-taxa-4(5),11(12)-dien-2-one) is an organic compound and a taxane. The compound is of some academic interest as a potential precursor to Taxol, in important anti-cancer drug, in a commercially viable process.[1] A total synthesis of taxadienone was reported in 2012 together with its conversion to the next Taxol precursor taxadiene.[2] A multigram synthetic method was reported in 2015.[3]

Taxadienone
Names
IUPAC name
Taxa-4,11-dien-2-one
Systematic IUPAC name
(4aS,6R,12aS)-4,9,12a,13,13-Pentamethyl-2,4a,6,7,8,11,12,12a-octahydro-6,10-methanobenzo[10]annulen-5(1H)-one
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C20H30O/c1-13-8-9-16-18(21)17-14(2)7-6-11-20(17,5)12-10-15(13)19(16,3)4/h7,16-17H,6,8-12H2,1-5H3/t16-,17-,20-/m0/s1
    Key: FNHWZFUZPRGYAH-ZWOKBUDYSA-N
  • [H][C@]12CCC(C)=C(CC[C@]3(C)CCC=C(C)[C@@]3([H])C1=O)C2(C)C
Properties
C20H30O
Molar mass 286.459 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References
  1. GEN News Highlights Nov 7, 2011 Scientists Develop Scalable Process for Synthesizing Diverse Taxanes http://www.genengnews.com/gen-news-highlights/scientists-develop-scalable-process-for-synthesizing-diverse-taxanes/81245919/
  2. Scalable enantioselective total synthesis of taxanes Abraham Mendoza, Yoshihiro Ishihara, Phil S. Baran Nature Chemistry 4, 21–25 (2012) doi:10.1038/nchem.1196
  3. Route Optimization and Synthesis of Taxadienone Sergiy G. Krasutsky, Sheila H. Jacobo, Scott R. Tweedie, Ravi Krishnamoorthy, and Alexander S. Filatov Organic Process Research & Development 2015 19 (1), 284-289 doi:10.1021/op500314c


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