Chiral Total Synthesis of (+)-Montbretyl12-Methyl Ether and (-)-Montbretyl12-Methyl Ether

Abstract

Abstract: By using (S)-(-)-α-cyclocitral(9a) and(R)-(+)-α-cyclocitral(9b)-obtained by chemical resolution as the Aring synthon, and triphenyl phosphonium chloride(18)-obtained from p bromoanisole via eight steps as the Cring synthon, the sole trans key intermediate 3 was obtained after the condensation and intracyclization reactions. The structure modification, (+)-montbretyl-12-methyl ether(1a)-and-(-)-montbretyl-12 methyl ether(1b) were obtained enantioselectively. The cyclization reaction of BF3·Et₂Ois the key step.

Key words: Polyoxyaroma, Diterpene, Stereoselectivity, Enantiomer

CLC Number:

O629

TrendMD:

LI An-Pai, PENG Xiao-Shui, WU Xiao-Ming, WU Tong-Xing, PAN Xin-Fu . Chiral Total Synthesis of (+)-Montbretyl12-Methyl Ether and (-)-Montbretyl12-Methyl Ether[J]. Chem. J. Chinese Universities, 2001, 22(9): 1511.

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Chiral Total Synthesis of (+)-Montbretyl12-Methyl Ether and (-)-Montbretyl12-Methyl Ether

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