Tetrahedron

A total synthesis of (±)-zoapatanol and demethyl-ORF13811

PJ Kocieński, CJ Love, G Costello, DA Roberts

Index: Kocienski, Philip J.; Love, Christopher J.; Whitby, Richard J.; Costello, Gerard; Roberts, David A. Tetrahedron, 1989 , vol. 45, # 12 p. 3839 - 3848

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Citation Number: 60

Abstract

Total syntheses of the spasmogenic diterpenoid zoapatanol and a demethyl analogue of the potent antigestational agent ORF 13811 are reported. A Ni0-catalysed coupling of MeMgBr with a dihydrofuran, and a carbo-or hydro-magnesiation of an acetylene were used to construct the tri-substituted alkenes in the key intermediates with high stereoselectivity.