Studies Towards a Total Synthesis of Amphidinolide B. Stereocontrolled Synthesis of the C14-C26 Polyol Fragment

M. Belén Cid; Gerald Pattenden

doi:10.1055/s-1998-1701

Synlett 1998; 1998(5): 540-542
DOI: 10.1055/s-1998-1701

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Studies Towards a Total Synthesis of Amphidinolide B. Stereocontrolled Synthesis of the C14-C26 Polyol Fragment

M. Belén Cid^* , Gerald Pattenden

^*Chemistry Department, Nottingham University, Nottingham NG7 2 RD, England

Abstract

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A practical synthesis of the C₁₄-C₂₆ polyol unit 2 in amphidinolides B₁ and B₂, 1, is described which involves elaboration of the chiral unsaturated aldehyde 4 and the chiral ketone 5, followed by crossed-aldolisation of 4 and 5 in the presence of LiHMDS at -78 °C, as key steps.

Sharpless asymmetric epoxidation - silylstannylation - Sharpless asymmetric dihydroxylation - crossed-aldolisation

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