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Total synthesis of (s)-(-) and (r)-(+)-frontalin and of (-)-malyngolide from the branched-chain sugar “α”-d-isosaccharino-lactone as chiral template

1988; Elsevier BV; Volume: 44; Issue: 21 Linguagem: Inglês

10.1016/s0040-4020(01)90101-2

1464-5416

Minh-Chau Trinh, Jean‐Claude Florent, Claude Monneret,

Carbohydrate Chemistry and Synthesis

Highly enantiomerically pure. (S)-(-) 2 and (R )-(+)-frontalin 3 and (-) -malyngolide. 4 were synthesized from the common chiral building block, ( 2R) -1, 2-O-isopropylidene-2-hydroxymethyl-pent-4-ene.-1, 2-diol 9 readily prepared in five. steps and 35% overall yield from α-D-isosaccharino-1 ,4-lactone 1.