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Facile asymmetric construction of a functionalized dodecahydrobenz[a]indolo[3,2-h]quinolizine template

journal contribution
posted on 08.11.2011 by Steven M. Allin, Liam J. Duffy, Joannah M.R. Towler, Philip C. Bulman Page, Mark Elsegood, Basu Saha
We report a highly diastereoselective approach for the synthesis of a functionalized dodecahydrobenz[a]indolo[3,2-h]quinolizine ring system that is present as the heterocyclic core of the manadomanzamine alkaloids. We have achieved complete control over the relative and absolute stereochemistries at the three contiguous stereocentres at ring positions 1, 10 and 24 in only two linear synthetic steps. The introduction of useful functionality to the heterocyclic skeleton is significant as this may allow for future derivatization, and application of this route in an asymmetric synthesis of the manadomanzamine natural products.

History

School

  • Aeronautical, Automotive, Chemical and Materials Engineering

Department

  • Chemical Engineering

Citation

ALLIN, S.M. ... et al, 2009. Facile asymmetric construction of a functionalized dodecahydrobenz[a]indolo[3,2-h]quinolizine template. Tetrahedron, 65 (49), pp. 10230-10234

Publisher

© Elsevier

Version

VoR (Version of Record)

Publication date

2009

Notes

This article is Closed Access, it was published in the journal, Tetrahedron [© Elsevier]. The definitive version is available from: http://www.sciencedirect.com/science/article/pii/S0040402009014689

ISSN

0040-4020

Language

en

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