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Total synthesis of (−)-verrucarol, a component of naturally occurring verrucarin A

✍ Scribed by Jun Ishihara; Rie Nonaka; Yuki Terasawa; Ryota Shiraki; Kazuo Yabu; Hiromi Kataoka; Yuichi Ochiai; Kin-ichi Tadano

Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 251 KB
Volume: 38
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(97)10209-x

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✦ Synopsis

Total synthesis of (-)-verruearol (1) was achieved starling from D-glucose-derived bicyclic lactone 4 through l) a stereoselective asymmetric quatemization of the a-carbon of the lactone, 2) Dieckmann cyclization for access to the C-ring equivalent, 3) a skeletal rearrangement for the trichothecene ring system, and 4) the final stereoselective epoxidation of an exo-methylene group.

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