166533-83-1Relevant academic research and scientific papers
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 (1998)
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.
New strategy for the synthesis of the taxane diterpenes: Formation of the A-ring and introduction of the C-1 hydroxyl group
Magnus, Philip,Booth, John,Magnus, Nicholas,Tarrant, James,Thom, Stephen,Ujjainwalla, Feroze
, p. 5331 - 5334 (2007/10/02)
The A-ring of the taxanes is conveniently made from an ester-sulfone condensation, and is compatible with the 1-hydroxyl group, thus completing the synthesis of the ABC-rings.
