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Aphidicolin synthesis (II)—an expeditious and efficient formal synthesis of (±)-aphidicolin

✍ Scribed by Masahiro Toyota; Youichi Nishikawa; Keiichiro Fukumoto

Publisher: Elsevier Science
Year: 1994
Tongue: French
Weight: 941 KB
Volume: 50
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(01)89418-7

No coin nor oath required. For personal study only.

✦ Synopsis

An expeditious and efftcient formal total synthesis of an antiviral and antitumor tetracyclic diterpene aphidicolin (1) has been achieved. An intramoleculat Heck reaction (74) and an intramolecular Diels-Aldex reaction (4+3) were utilii for the key steps of the sequence.

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## Abstract A simple, efficient, and stereospecific total synthesis of (±)‐3α, 18‐dihydroxy‐17‐noraphidicolan‐16‐one **(2)**, by solvolytic rearrangement of the __endo__‐bicyclo‐[2.2.2]oct‐5‐en‐2‐yl methanesulfonate **16**, is described. Since aphidicolin **(1)** has already been obtained from **2*