Asymmetric synthesis with. alpha.,. beta.-bis [(methoxymethyl) oxy] ketones. Enantioselective total synthesis of natural (+)-indolizidine 195B (bicyclic gephyrotoxin …

N Yamazaki, C Kibayashi

Index: Yamazaki, Naoki; Kibayashi, Chihiro Journal of the American Chemical Society, 1989 , vol. 111, # 4 p. 1396 - 1408

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Citation Number: 93

Abstract

Abstract: The first enantioselective total synthesis of naturally occurring (+)-indolizidine 195B (bicyclic gephyrotoxin 195B) and (-)-phidine and their enantiomers has been achieved starting from 4-0-benzyl-2, 3-0-bis (methoxymethyl)-~-threitol as a single and common chiral synthon, readily available from L-tartaric acid. This synthesis establishes the absolute stereochemistry of (+)-indohidine 195B as 3S, 5S, 9S. The strategy for the synthesis of the ...