1374036-48-2Relevant academic research and scientific papers
Synthesis of the macrolactone core of (+)-neopeltolide by transannular cyclization
Sharma, Gangavaram V.M.,Reddy, Sheri Venkat,Ramakrishna, Kallaganti V.S.
, p. 3689 - 3695 (2012/06/01)
The synthesis of the macrolactone core of (+)-neopeltolide has been achieved. The key synthetic strategy involves the highly diastereoselective synthesis of the 2,6-cis-disubstituted tetrahydropyran ring by a transannular cyclization of δ-hydroxy alkene using mercuric trifluoroacetate. Two of the six stereocenters C-5 and C-11 were realized from l-malic acid, while the remaining stereocenters C-3 (Sharpless asymmetric epoxidation), C-7 (transannular cyclization), C-9 (regioselective epoxide opening) and C-13 (chelation controlled reduction) were derived by asymmetric synthesis. The macrolactone ring was synthesized by macrocyclization using a RCM protocol.
