Synthetic Study of (-)-Norzoanthamine: Construction of the ABC Ring Moiety

被引：43

作者：

Murata, Yoshihisa ^{[1
]}

Yamashita, Daisuke ^{[1
]}

Kitahara, Katsushi ^{[1
]}

Minasako, Yohei ^{[1
]}

Nakazaki, Atsuo ^{[1
]}

Kobayashi, Susumu ^{[1
]}

机构：

[1] Tokyo Univ Sci, Fac Pharmaceut Sci, Noda, Chiba 2788510, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 08期

关键词：

diastereoselectivity; Diels-Alder reaction; Michael addition; natural products; total synthesis; ORGANIC-SYNTHESIS; ZOANTHAMINE/NORZOANTHAMINE ALKALOIDS; PHENYLDIMETHYLSILYL GROUP; CONVERSION; DIELS; NORZOANTHAMINE;

D O I：

10.1002/anie.200804544

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Throw your hat in the ring: A highly diastereoselective synthesis of the ABC rings of (-)-norzoanthamine has been achieved starting from the (-)-Hajos-Parrish ketone (see scheme). Three asymmetric quaternary carbon centers on the C ring were constructed by a 1,4-addition, and an intramolecular Diels-Alder reaction provided a trans-decalin scaffold on the AB rings. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：1400 / 1403

页数：4

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