Synthetic Study of Piericidins. I. Synthesis of the Side Chain of Piercidin B1

Machiko ONO; Norio YOSHIDA; Yuki KOKUBU; Eiji SATO; Hiroyuki AKITA

doi:10.1248/cpb.45.1428

Synthetic Study of Piericidins. I. Synthesis of the Side Chain of Piercidin B₁

Machiko ONO, Norio YOSHIDA, Yuki KOKUBU, Eiji SATO, Hiroyuki AKITA

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Keywords: piericidin B₁ side chain, Julia coupling, reductive olefin-formation, β, γ-unsaturated aldehyde, (E, Z)-olefin-isomerization

JOURNAL FREE ACCESS

1997 Volume 45 Issue 9 Pages 1428-1434

DOI https://doi.org/10.1248/cpb.45.1428

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Abstract

The side chain of piericidin B₁ having four (E)-olefinic linkages was prepared. The coupling reaction of the non-conjugated aldehyde (22) derived from 4, 4-dimethoxy-2-butanone and the sulfone (13) afforded a diastereomeric mixture of the hydroxy sulfone (27). Benzoylation of 27 followed by reductive olefin formation with sodium amalgam gave the desired all-trans-tetraene (29) possessing an (E)-C(5)-C(6) double bond, which was transformed to the alcohol (1) corresponding to the side chain of piericidin B₁.

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