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Base-Mediated Cascade Cyclization: Stereoselective Synthesis of Benzooxazocinone

Author:
Pramthaisong, Chiranan, Worayuthakarn, Rattana, Pharikronburee, Vannapha, Duangthongyou, Tanwawan, Rattanakam, Ramida, Ruchirawat, Somsak, Thasana, Nopporn
Source:
Organic letters 2018 v.20 no.13 pp. 4015-4019
ISSN:
1523-7052
Subject:
chemical bonding, chemical structure, coumarin, cyclization reactions, stereoselective synthesis
Abstract:
A new strategy for the synthesis of the oxa-azabicyclo[3.3.1]nonane subunit, a component of the naucleamide E core structure, has been developed. This annulation reaction between 1-substituted 3,4-dihydroisoquinolines and coumarin derivatives conveniently affords the oxa-azabicyclo[3.3.1]nonane framework via a base-mediated cascade cyclization under aqueous conditions. The value of this work lies in the efficient formation of the oxa-azabicyclo[3.3.1]nonane skeleton via a process whereby all the C–C, C–O, and C–N bond formations occur in a single chemical operation. In addition, the subsequent ring opening of these compounds furnished pyridoisoquinoline derivatives.
Agid:
6084190