A synthetic approach to zoapatanol and related bicyclic analogues

…, C Yeates, P Kocieński, G Costello

Index: Whitby, Richard; Yeates, Clive; Kocienski, Philip; Costello, Gerard Journal of the Chemical Society, Chemical Communications, 1987 , # 6 p. 429 - 430

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Citation Number: 7

Abstract

A Ni0-catalysed coupling of MeMgBr with dihydrofuran (4) and addition of Grignard reagent (7) to a butyne-1, 4-diol derivative (8) were key steps in the highly stereoselective construction of the trisubstituted double bonds in (10) which is a precursor to the oxepane ring system (12) of zoapatanol (1); subsequent elaboration of (12) gave (1R*, 4S*, 5R*)-4-[5- oxo-8-methylnon-7-enyl]-3, 8-dioxabicyclo [3.2. 1] octane-1-acetic acid (18), a demethyl ...