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Title: Facile asymmetric construction of a functionalized dodecahydrobenz[a]indolo[3,2-h]quinolizine template
Authors: Allin, Steven M.
Duffy, Liam J.
Towler, Joannah M.R.
Page, Philip C. Bulman
Elsegood, Mark R.J.
Saha, Basu
Keywords: Natural product
Heterocyclic
Acyliminium
Asymmetric
Cyclization
Issue Date: 2009
Publisher: © Elsevier
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
Abstract: 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.
Description: 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
Version: Published
DOI: 10.1016/j.tet.2009.09.097
URI: https://dspace.lboro.ac.uk/2134/9052
Publisher Link: http://www.sciencedirect.com/science/article/pii/S0040402009014689
ISSN: 0040-4020
Appears in Collections:Closed Access (Chemical Engineering)

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