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Formal total synthesis of 2-pupukeanone via radical mediated cyclisation of an enyne

Srikrishna, A and Vijaykumar, D and Sharma, GVR (1999) Formal total synthesis of 2-pupukeanone via radical mediated cyclisation of an enyne. In: Indian Journal of Chemistry Section B-Organic Chemistry Including Medicinal Chemistry, 38 (7). pp. 766-770.

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Official URL: http://nopr.niscair.res.in/handle/123456789/60

Abstract

Diels-Alder reaction of the dienone 12, obtained by C-alkylation of sodium 2,6-dimethylphenoxide, with acrylonitrile and phenyl vinyl sulfones generate the enynes 14 and 17. Tributyltin radical addition to the terminal acetylene in 14 and 17 lead to the vinylstannanes 15 and 18 via 5-exo trig cyclisation of the resulting vinyl radical, which on oxidative cleavage furnishes the isotwistane-diones 16 and 19. Reductive desulfonylation of the diketosulfone 19 furnishes the dione 11, constituting a formal total synthesis of 2-pupukeanone 5 and 2-isocyanopupukeanone 3.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to National Institute of Science Communication and Information Resources.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 22 Jul 2009 07:59
Last Modified: 22 Jul 2009 07:59
URI: http://eprints.iisc.ernet.in/id/eprint/19518

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