Synthesis of (±)-2-methoxy-9a-carbamorphinan and (±)-2-methoxy-9a-carba-14α-morphinan: acid catalyzed cyclizations of 1-m̲-methoxybenzyl-4, 4a,5,6,7,8-hexahydronaphthalen-2(3H)-one and 1-m̲-methoxy benzyloctalins

Pal, Sitaram ; Ghosh, Sukumar ; Banik, Bimal K. ; Alam, Shaikh Khairul ; Ghatak, Usha Ranjan (1990) Synthesis of (±)-2-methoxy-9a-carbamorphinan and (±)-2-methoxy-9a-carba-14α-morphinan: acid catalyzed cyclizations of 1-m̲-methoxybenzyl-4, 4a,5,6,7,8-hexahydronaphthalen-2(3H)-one and 1-m̲-methoxy benzyloctalins Synthetic Communications, 20 (14). pp. 2203-2216. ISSN 0039-7911

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Related URL: http://dx.doi.org/10.1080/00397919008053160

Abstract

The bridged-ethers, (±)-2-methoxy-9a-carbamorphinan (1b) and (±)-2-methoxy-9a-carba-14α -morphinan(2b) have been synthesized. The acid-catalyzed cyclizations of 1-m̲-methoxy benzyloctalone 3b and 1-m̲-methoxybenzyloctalins 4b proceed with high regio-and stereoselectivities leading mostly to the bridged-ketone 14 and ether 1b respectively, along with o̲-methoxy-tetracyclic ketone 15 and the ether 17, in addition to other minor products.

Item Type:	Article
Source:	Copyright of this article belongs to Taylor and Francis Ltd.
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Deposited On:	15 Dec 2010 12:25
Last Modified:	17 May 2016 11:16

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