Exploiting multiple nucleophilic sites on pyrrole for the assembly of polyheterocyclic frameworks:: application to a formal total synthesis of (±)-aspidospermidine

被引：40

作者：

Banwell, MG ^{[1
]}

Smith, JA ^{[1
]}

机构：

[1] Australian Natl Univ, Inst Adv Studies, Res Sch Chem, Canberra, ACT 0200, Australia

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2002年 / 23期

关键词：

D O I：

10.1039/b208821e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The tricyclic ketone 19, an advanced intermediate in Aube's recently reported synthesis of aspidospermidine (4), is prepared in twelve steps from pyrrole (3). The key transformations involve a previously described intramolecular Michael addition reaction of pyrrole 10 and intramolecular Friedel-Crafts type cyclisation of the derived carboxylic acid 15 to ketone 16. Careful hydrogenation of this last compound afforded the fully saturated alcohol 17 which was readily oxidised to the target ketone 19.

引用

页码：2613 / 2618

页数：6

共 38 条

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