Tetrahedron letters

Acyclic stereoselection. 19. Total synthesis of (±)-ristosamine and (±)-megalosamine.

CH Heathcock, SH Montgomery

Index: Heathcock, Clayton H.; Montgomery, Stephen H. Tetrahedron Letters, 1983 , vol. 24, # 43 p. 4637 - 4640

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Citation Number: 13

Abstract

Abstract (±)-Ristosamine (1) has been synthesized in seven straightforward operations from ketone 5 and O-benzyllactaldehyde. The key step is a stereoselective aldol addition reaction in which diastereomeric aldols 7 and 8 are produced in a ratio of 78: 22. A simple modification of the synthesis provides (±)-megalosamine (4.