Tetrahedron: Asymmetry

Total synthesis of (+)-asperlin

H Akaike, H Horie, K Kato, H Akita

Index: Akaike, Hideaki; Horie, Hidekazu; Kato, Keisuke; Akita, Hiroyuki Tetrahedron Asymmetry, 2008 , vol. 19, # 9 p. 1100 - 1105

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Citation Number: 14

Abstract

Syntheses of (+)-asperlin 1 were achieved via two different synthetic routes. 1, 2-Addition of α-furyl anion to (2R, 3S)-2-tbutyldimethylsilyloxy-3-chlorobutanal 6 gave (1S, 2R, 3S)-1-(2- furyl)-2-tbutyldimethylsilyloxy-3-chlorobutanol 7, which was converted to the chiral intermediate,(1S, 2R, 3R)-1-(2-furyl)-2, 3-epoxybutanol 8 (37% overall yield from 6) for the synthesis of (+)-1. The second synthesis of (+)-asperlin 1 from (2R, 3S)-6 was achieved in ...

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