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Functionalization of the 6,14-Bridge of the Orvinols : 1. Preparation and Diels–Alder Reaction of 7-Phenylsilylthebaines

✍ Scribed by Weibin Chen; Damon A. Parrish; Jeffrey R. Deschamps; Andrew Coop

Book ID
102260146
Publisher
John Wiley and Sons
Year
2005
Tongue
German
Weight
104 KB
Volume
88
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The anion 5 of thebaine (1) reacts with small electrophiles exclusively at the 5‐position (Scheme 1). Reaction of thebaine anion with a range of alkylarylsilyl chlorides showed that reaction at the 7‐position was favored with increasing steric bulk, with triphenylsilyl chloride yielding only the 7‐substituted product 7e (Scheme 1). Reaction of 7‐(triphenylsilyl)thebaine (7e) with benzoquinone gave rise to the expected Diels–Alder adduct 8 (Scheme 2), an analog of thevinone (2) with a silyl substituent at the 6,14‐etheno bridge. The presence of this substituent gives a handle for potentially functionalizing the bridge of this important class of compounds.

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