Tetrahedron

Synthesis and structural elucidation of a new zooecdysteroid gerardiasterone

M Tsubuki, H Takada, T Katoh, S Miki, T Honda

Index: Tsubuki, Masayoshi; Takada, Hironao; Katoh, Tadashi; Miki, Shigehiro; Honda, Toshio Tetrahedron, 1996 , vol. 52, # 46 p. 14515 - 14532

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Citation Number: 10

Abstract

The first synthesis of a new zooecdysteroid gerardiasterone was achieved in a diastereoselective manner employing asymmetric dihydroxylation of the E-olefin 34 in the presence of DHQ-CLB as a chiral ligand. This synthesis unambiguously confirmed the structure of gerardiasterone as (20R, 22R, 23S)-2β, 3β, 14α, 20, 22, 23, 25-heptahydroxy-5β- cholest-7-en-6-one (2a).