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.
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