Syntheses of Taiwaniaquinone F and Taiwaniaquinol A via an Unusual Remote C-H Functionalization

被引：54
作者：
Thommen, Christophe [1 ]
Jana, Chandan Kumar [1 ]
Neuburger, Markus [1 ]
Gademann, Karl [1 ]
机构：
[1] Univ Basel, Dept Chem, CH-4056 Basel, Switzerland
来源：
ORGANIC LETTERS | 2013年 / 15卷 / 06期
关键词：
EFFICIENT ROUTE; DITERPENES; (+/-)-TAIWANIAQUINOL-B; (+/-)-DICHROANAL-B; STEREOCHEMISTRY; BIOSYNTHESIS; KETONIZATION; DERIVATIVES; QUINONES; CLEAVAGE;
D O I：
10.1021/ol4003652
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A protecting-group-free route to (-)-taiwaniaquinone F based on a ring contraction and subsequent aromatic oxidation of a sugiol derivative is reported. In addition, the first synthesis of (+)-taiwaniaquinol A is reported via short time exposure of (-)-taiwaniaquinone F to sunlight triggering a remote C-H functionalization. The hypothesis that the biogenesis of some methylenedioxy bridged natural products could proceed via similar nonenzymatic mechanisms is presented.
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页码：1390 / 1393
页数：4
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