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Synthesis of homochiral α-alkoxystannanes: stereospecific conversion to cembranolide precursors

✍ Scribed by James A. Marshall; Wei Yi Gung

Publisher
Elsevier Science
Year
1988
Tongue
French
Weight
278 KB
Volume
29
Category
Article
ISSN
0040-4039

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✦ Synopsis

Stannyl ketone 3 is reduced rapid1 Noyori's (Rl-( + l-BINAGH rea $ nt. The derive B and with high stereoselectivity to the @)-alcohol 4 by MOM ether aldehyde cyclises upon treatment with BF3 l Et.20 affording the cis alto 018 as a single enantiomer.

We recently described a facile cyclisation of the a-alkoxyallylstannane aldehyde I leading to the cembranolide precursor II as a co. 7:l mixture of cis and trans isomers in 88% yield.1 Alcohol II was further elaborated2 to the racemate of the unnamed cembranolide III.3

📜 SIMILAR VOLUMES

Stereoselective total synthesis of cembr
Stereoselective total synthesis of cembranolides through cyclizationof a homochiral (α-alkoxyallyl)stannane precursor
✍ James A. Marshall; Wei Yi Gung 📂 Article 📅 1988 🏛 Elsevier Science 🌐 French ⚖ 202 KB

The homochiral hydroxy enol ether 2, secured through BFa-promoted cyclization of alkoxy stannane 1, was elaborated to the unnamed cembranolide V, a constituent of a soft coral inhabitant of the Great Barrier Reef. The synthesis confirms the absolute stereochemistry of the natural product.