Highly regio- and diastereo-selective synthesis of novel tri- and tetra-cyclic perhydroquinoline architectures via an intramolecular [3+2] cycloaddition reaction

被引：35

作者：

Bakthadoss, M. ^{[1
,2
]}

Kannan, D. ^{[2
]}

Srinivasan, J. ^{[2
]}

Vinayagam, V. ^{[2
]}

机构：

[1] Pondicherry Univ, Dept Chem, Pondicherry 605014, India

[2] Univ Madras, Dept Organ Chem, Madras 600025, Tamil Nadu, India

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2015年 / 13卷 / 10期

关键词：

BAYLIS-HILLMAN REACTION; ASYMMETRIC 1,3-DIPOLAR CYCLOADDITION; PYRROLOQUINOLINE CORE; MARTINELLIC ACID; FORMAL SYNTHESIS; TETRAHYDROQUINOLINES; (+/-)-HELIOTRIDANE;

D O I：

10.1039/c4ob02203c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile and efficient synthetic protocol was established for the construction of novel tri- and tetra-cyclic pyrrolo/pyrrolizinoquinoline architectures via the in situ formation of azomethine ylide followed by an intramolecular [3 + 2] cycloaddition reaction strategy. This protocol leads to the creation of two/three new rings and three/four contiguous stereocentres, in which one of them is a tetra-substituted carbon center, in a highly diastereoselective fashion with excellent yields.

引用

页码：2870 / 2874

页数：5

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