Double Reduction of Cyclic Aromatic Sulfonamides: Synthesis of (+)-Mesembrine and (+)-Mesembranol

被引：33

作者：

Geoghegan, Kimberly ^{[1
]}

Evans, Paul ^{[1
]}

机构：

[1] Natl Univ Ireland Univ Coll Dublin, Sch Chem & Chem Biol, Ctr Synth & Chem Biol, Dublin 4, Ireland

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 07期

关键词：

SCELETIUM ALKALOIDS; QUATERNARY STEREOCENTERS; FORMAL SYNTHESIS; EFFICIENT; CONSTRUCTION; CYCLIZATIONS; CENTERS;

D O I：

10.1021/jo4000306

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of (+)-mesembrine (1) and (+)-mesembranol (2) has been achieved from the monoterpene (S)-(-)-perillyl alcohol. Key transformations include a diastereo- and regioselective Pd-mediated intramolecular Heck reaction, and a double reduction of the resultant cyclic sulfonamide, to afford the cis-3a-aryloctahydroindole skeleton.

引用

收藏

页码：3410 / 3415

页数：6

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