Stereospecific route to 5,11-methanomorphanthridine alkaloids via intramolecular 1,3-dipolar cycloaddition of nonstabilized azomethine ylide: formal total synthesis of (±)-pancracine

Pandey, Ganesh ; Banerjee, Prabal ; Kumar, Ravindra ; Puranik, Vedavati G. (2005) Stereospecific route to 5,11-methanomorphanthridine alkaloids via intramolecular 1,3-dipolar cycloaddition of nonstabilized azomethine ylide: formal total synthesis of (±)-pancracine Organic Letters, 7 (17). pp. 3713-3716. ISSN 1523-7060

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Official URL: http://pubs.acs.org/doi/abs/10.1021/ol051321o

Related URL: http://dx.doi.org/10.1021/ol051321o

Abstract

The core structure of the complex pentacyclic 5,11-methanomorphanthridine alkaloids is constructed stereospecifically in one step employing an intramolecular [3 + 2]-cycloaddition of nonstabilized azomethine ylide as the key step. The strategy is demonstrated by accomplishing the formal total synthesis of (± )-pancracine.

Item Type:Article
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ID Code:61016
Deposited On:13 Sep 2011 11:30
Last Modified:13 Sep 2011 11:30

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