Enantioselective Synthesis of MK-287

Abstract

Abstract: (2″S,5″S)-2-{3′-Methoxy-2′-propoxy-5′-[5″-(3′″,4′″,5′″-trimethoxyphenyl)tetrahydrofuran-2″-yl] phenylsulfonyl}ethanol(MK-287) which was potent PAF antagonist, was enantioselectively synthesized in eight steps by addition, oxidation, hot decomposition, hydrogenation and so on from (-)-4,10-dioxatricyclo-[5.2.1.0^2,6]-decene-3-ole(1). Asymmetry was introduced using the nucleophilic addition of the triisopropoxytitanium to the lactol 1. The second asymmetric center was installed by a highly stereocontrolled acid-assisted reduction with sodium cyanoborohydride of the hemiketal formed. The product MK-287 was optically pure.

Key words: Enantioselectivity, Chirality, MK-287

CLC Number:

O621
O641.6

TrendMD:

SHI Hong-Xin, LIN Hui, R. Bloch, G. Mandville . Enantioselective Synthesis of MK-287[J]. Chem. J. Chinese Universities, 2004, 25(5): 874.

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Enantioselective Synthesis of MK-287

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