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Stereoselective total synthesis of cembranolides through cyclizationof a homochiral (α-alkoxyallyl)stannane precursor

✍ Scribed by James A. Marshall; Wei Yi Gung

Publisher: Elsevier Science
Year: 1988
Tongue: French
Weight: 202 KB
Volume: 29
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)80375-5

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✦ Synopsis

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.

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Total synthesis of halichondrins: Highly

Total synthesis of halichondrins: Highly stereoselective construction of a homochiral pentasubstituted H-ring pyran intermediate from α-d-glucose

✍ Seokchan Kim; Robert G. Salomon 📂 Article 📅 1989 🏛 Elsevier Science 🌐 French ⚖ 190 KB

The functionality of a-D-Glucose is stereoselectively manipulated exploiting pyranose furanose ~ pyranose interconversions and lactonization for selective masking to achieve a stereocontrolled synthesis of the densely substituted H-ring pyran of halichondrins. Halichondrins0 a family of macrolide p