On the origin of quasi-racemic aplysinopsin cycloadducts, (bis)indole alkaloids isolated from scleractinian corals of the family Dendrophylliidae. Involvement of enantiodefective Diels-Alderases or asymmetric induction in artifact processes involving adventitious catalysts?

被引：41

作者：

Mancini, I ^{[1
]}

Guella, G

Zibrowius, H

Pietra, F

机构：

[1] Univ Trent, Chim Bioorgan Lab, I-38050 Trent, Italy

[2] Ctr Oceanol Marseille, Marine Endoume Stn, F-13007 Marseille, France

来源：

TETRAHEDRON | 2003年 / 59卷 / 44期

关键词：

(bis)indole alkaloids; Diels-Alder cycloaddition reactions; Diels-Alderases; chiral shift reagents; enantiomeric composition;

D O I：

10.1016/j.tet.2003.09.038

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reported here are two novel quasi-racemic (bis)indole alkaloids, cycloaplysinopsin A (5) and cycloaplysinopsin B (6), isolated from tropical Indo-Pacific (Comoros, Philippines) scleractinian corals of the family Dendrophylliidae. Although their structures suggest a Diels-Alder cycloaddition origin from aplysinopsin-type precursors, neither experiments, nor theory allowed us to clearly distinguish an enzymatic process with scarce enantioselection from the intrusion of an adventitious catalyst in the coral extracts, where the chiral environment caused a slight asymmetric induction. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：8757 / 8762

页数：6

共 18 条

[1]

[Anonymous], 1991, Comprehensive Organic Synthesis

[2] Lovastatin nonaketide synthase catalyzes an intramolecular Diels-Alder reaction of a substrate analogue [J].