Studies aimed at the total synthesis of azadirachtin. A modeled connection of C-8 and C-14 in azadirachtin.

Studies aimed at the total synthesis of azadirachtin. A modeled connection of C-8 and C-14 in azadirachtin.

Organic letters (2002-08-17)

Takehiro Fukuzaki, Satoshi Kobayashi, Takamasa Hibi, Yohei Ikuma, Jun Ishihara, Naoki Kanoh, Akio Murai

ABSTRACT

[reaction: see text] Studies on the connection between the right and left segments of azadirachtin are described. The Ireland-Claisen rearrangement of Li-enolate of the modeled ester with dichlorodimethylsilane in toluene afforded the desired limonoid framework stereoselectively in good yield.

MATERIALS

Product Number

Brand

Product Description

85126

Supelco

Silanization solution I, ~5% (dimethyldichlorosilane in heptane), Selectophore^™

440272

Sigma-Aldrich

Dichlorodimethylsilane, ≥99.5%

40140

Sigma-Aldrich

Dichlorodimethylsilane, ≥98.5% (GC)

80430

Sigma-Aldrich

Dichlorodimethylsilane, produced by Wacker Chemie AG, Burghausen, Germany, ≥99.0% (GC)