The total synthesis of (-)-connatusin A, a hirsutane-type sesquiterpene isolated from the fungus Lentinus connatus BCC8996

被引：28

作者：

Bon, David J. -Y. D. ^{[1
]}

Banwell, Martin G. ^{[1
]}

Cade, Ian A. ^{[1
]}

Willis, Anthony C. ^{[1
]}

机构：

[1] Australian Natl Univ, Inst Adv Studies, Res Sch Chem, Canberra, ACT 0200, Australia

来源：

TETRAHEDRON | 2011年 / 67卷 / 43期

基金：

澳大利亚研究理事会;

关键词：

Chemoenzymatic; Connatusin A; Diels-Alder; Oxa-di-pi-methane; Photochemistry; Sesquiterpene; CHEMOENZYMATIC TOTAL-SYNTHESIS; NATURAL-PRODUCTS; ACID; METHODOLOGY; PRECURSORS; CHEMISTRY; TOLUENE;

D O I：

10.1016/j.tet.2011.08.057

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The title sesquiterpenoid natural product 1 has been prepared for the first time using the enantiomerically pure cis-1,2-dihydrocatechol 3 as starting material. Key steps associated with the synthesis include a Diels-Alder cycloaddition reaction of the acetonide 5 with cyclopentenone (4) and an oxa-di-pi-methane rearrangement of bicylco[2.2.2]octenone 6 derived from the initial adduct. The product of this sequence, the cyclopropannulated triquinane 7, was elaborated, over a further eight steps including those involving Upjohn dihydroxylation and Swern oxidation protocols, to the target 1. A single-crystal X-ray analysis served to confirm the structure of this synthetically derived material. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：8348 / 8352

页数：5

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