Tetrahedron

Two syntheses of manoalide via heteroatom-assisted alkyne carbometallation

P Bury, G Hareau, P Kocieński, D Dhanak

Index: Bury, Paul; Hareau, Georges; Kocienski, Philip; Dhanak, Dashyant Tetrahedron, 1994 ,  vol. 50,  # 29  p. 8793 - 8808

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Citation Number: 42

Abstract

Two approaches to the sesterterpenoid phospholipase A2 inhibitors seco--manoalide (3) and manoalide (1) are described based on carbometallation of propargylic alcohols to generate the functionalised C6–C7 trisubstituted alkene. Both syntheses also deploy the photooxidation of a furan in order to generate a 4-substituted-5-hydroxy-2 (5H)-furanone moiety.