182236-70-0Relevant academic research and scientific papers
Isomerization, autooxidation and epimerization for the introduction of C-1 to C-5 functionality into the taxane ABC ring system
Magnus, Philip,Ujjainwalla, Feroze,Westwood, Nicholas,Lynch, Vince
, p. 6639 - 6642 (1996)
Treatment of 2-ketotax-3-enes with t-BuOK/t-BuOH/THF/65°C results in isomerization of the double bond into the 4,5-position and a trans-B/C ring fusion. Subsequent exposure to t-BuOK/THF/P(OEt)3 introduces the C-1-hydroxyl group.
Taxane diterpenes 4: Autoxidation, epimerization and isomerization for the introduction of functionality into the taxane ABC ring system
Magnus, Philip,Ujjainwalla, Feroze,Westwood, Nicholas,Lynch, Vince
, p. 3069 - 3092 (2007/10/03)
The bicyclo[5.4.0]undecenone 4 was converted through a four step sequence involving activation, gemmethylcyclopropanation and reductive cleavage into 18α/β, containing the B/C rings of the taxanes. The A-ring has been attached to the B/C ring system by cyclization of the sulfone-ester 23α to give 24. The A-ring was modified to give 29, which underwent β- elimination of the 3,10-oxido bridge via a dianion, followed by transannular hydride shift to give the butenolide 30 and 32. Autoxidation of 30 gave 33 which was further elaborated into the transfused B/C adduct 35. The isomeric 3,10-diones trans-39 and cis-45 undergo autoxidation using t- BuOK/THF/O2/P(OEt)3 to give 2 and 46 respectively without B/C cis/trans isomerization.
