Total synthesis of granditropone, grandirubrine, imerubrine, and isoimerubrine

被引：52

作者：

Boger, DL

Takahashi, K

机构：

[1] Department of Chemistry, The Scripps Research Institute, La Jolla, California 92037

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1995年 / 117卷 / 50期

关键词：

D O I：

10.1021/ja00155a009

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Concise total syntheses of the naturally occurring tropoloisoquinolines grandirubrine (1), imerubrine (2), and isoimerubrine (3) are detailed. The regioselective total synthesis of grandirubrine (1) is based on the [4 + 2] cycloaddition reaction of the alpha-pyrone 44 with the cyclopropenone ketal 18. Subsequent retro-Diels-Alder loss of CO2, norcaradiene rearrangement to the cycloheptatrienone ketal, and ketal hydrolysis provided the tropone 7 (granditropone). Regioselective hydroxylation of granditropone (NH2NH2; KOH) provided grandirubrine (1) and O-methylation of 1 provided both imerubrine (2) and isoimerubrine (3).

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页码：12452 / 12459

页数：8

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