Total Synthesis of (±)-19-Norabieta-4(18),8,11,13-tetraen-7-one

Abstract

Abstract: (±)-19-Norabieta-4(18),8,11,13-tetraen-7-one(8) was first synthesized starting from m-isopropylbromobenzene(1). After bromination of alcohol(2), coupling reaction of bromide(3) with Hagemann′s ester in the presence of t-BuOK and hydrolysis of compound(4) with KOH, compound (5) was obtained in a high yield. Intramolecular cyclization of coupling compound(5) with BF₃·Et₂O afforded a trans-fused key intermediate(6). After structural modification by Wittig reaction with Ph₃P +CH₃I-and oxidation with CrO₂, the target molecule was obtained in a good yield.

Key words: Tricyclic diterpene, Total synthesis, Natural product

CLC Number:

O629

TrendMD:

BIE Ping-Yan, ZHANG Cheng-Lu, PENG Xuan-Jia, CHEN Bo, YANG Yi, PAN Xin-Fu . Total Synthesis of (±)-19-Norabieta-4(18),8,11,13-tetraen-7-one[J]. Chem. J. Chinese Universities, 2003, 24(7): 1219.

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Total Synthesis of (±)-19-Norabieta-4(18),8,11,13-tetraen-7-one

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