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Facile asymmetric construction of a functionalized dodecahydrobenz[a]indolo[3,2-h]quinolizine template
journal contribution
posted on 2011-11-08, 14:14 authored by Steven M. Allin, Liam J. Duffy, Joannah M.R. Towler, Philip C. Bulman Page, Mark ElsegoodMark Elsegood, Basu SahaWe 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. 10230-10234Publisher
© ElsevierVersion
- VoR (Version of Record)
Publication date
2009Notes
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/S0040402009014689ISSN
0040-4020Publisher version
Language
- en