Organic & biomolecular chemistry

Efficient and highly enantioselective formation of the all-carbon quaternary stereocentre of lyngbyatoxin A

P Vital, D Tanner

Index: Vital, Paulo; Tanner, David Organic and Biomolecular Chemistry, 2006 , vol. 4, # 23 p. 4292 - 4298

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Citation Number: 10

Abstract

Indole 25, an advanced intermediate in a projected enantioselective total synthesis of lyngbyatoxin A 1, was prepared from allylic alcohol 11 in 9 steps and> 95% ee, key transformations being the enantiospecific rearrangement of vinyl epoxide 14 and the Hemetsberger–Knittel reaction of azide 24.