Base-Dependent Divergent Annulation of 4-Chloro-3-formylcoumarin and Tetrahydroisoquinoline: Application to the Synthesis of Isolamellarins and Hydroxypyrrolones

A series of pyrrolo[2,1-a]isoquinoline and coumarin-fused pentacyclic derivatives were synthesized via base-mediated divergent annulation of 4-chloro-3-formylcoumarin and tetrahydroisoquinoline as a key step. This method was then extended to the preparation of isolamellarins A and B (isolamellarin G...

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Bibliographic Details
Published in:Journal of organic chemistry Vol. 84; no. 6; pp. 3662 - 3670
Main Authors: Vyasamudri, Sameer, Yang, Ding-Yah
Format: Journal Article
Language:English
Published: WASHINGTON Amer Chemical Soc 15.03.2019
Subjects:
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
LAMELLARIN-ALPHA 20-SULFATE
CHILENINE
INHIBITORS
DERIVATIVES
ALKALOIDS
ISSN:0022-3263, 1520-6904, 1520-6904
Online Access:Get more information
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Summary:A series of pyrrolo[2,1-a]isoquinoline and coumarin-fused pentacyclic derivatives were synthesized via base-mediated divergent annulation of 4-chloro-3-formylcoumarin and tetrahydroisoquinoline as a key step. This method was then extended to the preparation of isolamellarins A and B (isolamellarin G trimethyl ether). When exposed to UV light, the pyrrolo[2,1-a]isoquinoline- and coumarin-fused pentacycles B were found to undergo aerobic oxidation to give the corresponding hydroxypyrrolones.
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ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.8b03259