Palladium-catalysed intramolecular arylation: a new synthesis of munduserone

PC Amos, DA Whiting

Index: Amos, Peter C.; Whiting, Donald A. Journal of the Chemical Society, Chemical Communications, 1987 , # 7 p. 510 - 511

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Citation Number: 10

Abstract

Treatment of the aryl iodides (11) with palladium acetate gave the tetracyclic stilbenes (13) via a formal but stereochemically disallowed Heck reaction; the method was exploited to synthesise (2)-munduserone (21). ... Aryl iodides of general type (1) would, under the conditions of the Heck reaction, be expected to generate an aryl palladium species (2), leading on through syn addition to an intermediate (3). This intermediate would lack the syn Pd-H stereochem- istry ...