Tetrahedron: Asymmetry

Asymmetric synthesis of (3S, 4R, 7S)-(−)-3-hydroxy-7-methoxy-2, 2, 4-trimethyl-decanoic acid, a plausible polyketide fragment of halipeptin A

C Della Monica, N Maulucci, F De Riccardis…

文献索引：Della Monica, Carmela; Maulucci, Nakia; De Riccardis, Francesco; Izzo, Irene Tetrahedron Asymmetry, 2003 , vol. 14, # 21 p. 3371 - 3378

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被引用次数: 7

摘要

The first enantioselective synthesis of (3S, 4R, 7S)-(−)-3-hydroxy-7-methoxy-2, 2, 4-trimethyl- decanoic acid 4 in 11 steps and 6% overall yield, starting from commercially available methyl 2, 2-dimethyl-3-hydroxy propionate 5 is described. The stereochemical flexible synthetic pathway involves a Brown's crotylboration reaction and a Corey–Bakshi–Shibata (CBS) oxazaborolidine-mediated reduction.