Stereoselective synthesis of (-)-amphidinolide E.
The total synthesis of (-)-amphidinolide E was accomplished by following a synthetic scheme that incorporates the labile C2 stereocenter at a very late stage. The oxolane unit was prepared by beta-alkoxyacrylate radical cyclization. The enyne metathesis reaction was employed for the synthesis of the side chain. The Kocienski-Julia reaction was used for the union of the two major fragments, and the Kita macrolactonization protocol was used for macrolide synthesis.
Kim
Chan Hyuk
CH
Department of Chemistry, Seoul National University, Seoul 151-747, Korea.
An
Hyo Jung
HJ
Shin
Won Kyo
WK
Yu
Wei
W
Woo
Sang Kook
SK
Jung
Soon Kyu
SK
Lee
Eun
E
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D004951:Esterification; D005609:Free Radicals / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D000097442:Amphidinolides
D019086:Bridged Bicyclo Compounds, Heterocyclic; D005609:Free Radicals; C452448:amphidinolide E; D000097442:Amphidinolides