Total Synthesis of (±)-α-Chamigrene-3-one

Chem. J. Chinese Universities ›› 2003, Vol. 24 ›› Issue (10): 1820.

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Total Synthesis of (±)-α-Chamigrene-3-one

WANG Jin-Jun¹, YIN Jun-Gang¹, WU Xu-Ran¹, ZHAO Yan¹, TAKESHITA Histoshi², MORI Akira², HATSUI Toshihide²

1. Department of Applied Chemistry, Yantai University, Yantai 264005, China;
2. Institute of Advanced Material Study, Kyushu University, Kyushu, Japan

Received:2002-09-19 Online:2003-10-24 Published:2003-10-24

Abstract

Abstract: In this paper, (±)-α-chamigrene-3-one, a spiro-sesquiterpenoid isolated from Marchantia polymorpha, was synthesized via a useful synthon in the synthesis of chamigrene-type sesquiterpenes, i.e., 1,5,5-trimethyl^-1-methoxycarbonylspiroundeca -1,8-dien-3-one(6).This precursor was obtained by the de Mayo reaction of terpinolene with methyl 2,4-dioxopentanoate, followed by the retro-aldol rearrangement of the proto-photocyclo-adducts and then Claisen condensation.The title compound was prepared via compound 6 by further transformed by chemical modification at the functional groups

Key words: Spiro-compound, Sesquiterpenoids, (±)-α-Chamigrene, (±)-α-Chamigrene-3-one, Total synthesis

CLC Number:

O621.3

TrendMD:

WANG Jin-Jun, YIN Jun-Gang, WU Xu-Ran, ZHAO Yan, TAKESHITA Histoshi, MORI Akira, HATSUI Toshihide . Total Synthesis of (±)-α-Chamigrene-3-one[J]. Chem. J. Chinese Universities, 2003, 24(10): 1820.

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Total Synthesis of (±)-α-Chamigrene-3-one

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