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Base-Mediated Cascade Cyclization: Stereoselective Synthesis of Benzooxazocinone

Base-Mediated Cascade Cyclization: Stereoselective Synthesis of Benzooxazocinone

Chiranan Pramthaisong, Rattana Worayuthakarn, Vannapha Pharikronburee, Tanwawan Duangthongyou, Ramida Rattanakam, Somsak Ruchirawat, Nopporn Thasana

Org Lett. 2018 Jul 6;20(13):4015-4019.

PMID: 29939032

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP111842	Nonane		111-84-2	Price

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