Tetrahedron

The synthesis of a natural product family: from debromoisolaurinterol to the aplysins

DC Harrowven, MC Lucas, PD Howes

Index: Harrowven, David C; Lucas, Matthew C; Howes, Peter D Tetrahedron, 2001 , vol. 57, # 4 p. 791 - 804

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Citation Number: 49

Abstract

Total syntheses of (±)-aplysin 1,(±)-debromoaplysin 2,(±)-isoaplysin 3,(±)-aplysinol 4,(±)- debromoaplysinol 5,(±)-aplysinal 6,(±)-isolaurinterol 7 and (±)-debromoisolaurinterol 8 are described. Key features are a diastereoselective, sulfur mediated radical cyclisation of diene 12 to give 35; a new radical to polar crossover sequence mediated by Bu3Sn that transforms diene 12 into (±)-debromoisolaurinterol 8; and a series of biomimetic cyclisation and ...