Synthesis of the trans-hydrindane core of dictyoxetane

被引：27
作者：
Defaut, Benedicte [1 ]
Parsons, Thomas B. [1 ]
Spencer, Neil [1 ]
Male, Louise [1 ]
Kariuki, Benson M. [1 ]
Grainger, Richard S. [1 ]
机构：
[1] Univ Birmingham, Sch Chem, Birmingham B15 2TT, W Midlands, England
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2012年 / 10卷 / 25期
基金：
英国工程与自然科学研究理事会;
关键词：
MICHAEL-TYPE ALKYLATION; ENANTIOSELECTIVE SYNTHESIS; CONCISE SYNTHESIS; BUILDING-BLOCK; EXPEDITED APPROACH; CARBONYL-COMPOUNDS; HAJOS DIONE; CONSTRUCTION; STRATEGY; ROUTE;
D O I：
10.1039/c2ob25384d
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A concise, stereoselective synthesis of the trans-hydrindane core of the marine natural product dictyoxetane is reported, starting from a Robinson annelation derived bicyclic enone. A phosphorane-mediated, pinacol-like rearrangement of a cis-diol, via a formal 1,2-hydride shift, is used to establish the requisite trans ring junction. P-31 NMR supports the formation of the intermediate phosphorane, generated in situ from the reaction of a diol with Ph3PCl2.
引用
收藏
页码：4926 / 4932
页数：7
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