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  • 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
PMID12182578
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
440272
Sigma-Aldrich
Dichlorodimethylsilane, ≥99.5%
Pricing and availability is not currently available.
80430
Sigma-Aldrich
Dichlorodimethylsilane, Wacker Chemie AG, ≥99.0% (GC)
Pricing and availability is not currently available.
40140
Sigma-Aldrich
Dichlorodimethylsilane, ≥98.5% (GC)
Pricing and availability is not currently available.
85126
Supelco
Silanization solution I, ~5% (dimethyldichlorosilane in heptane), Selectophore™
Pricing and availability is not currently available.