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

Steven M. Allin, Liam J. Duffy, Joannah M.R. Towler, Philip Bulman Page, Mark R. J. Elsegood, Basu Saha

Research output: Contribution to journalArticlepeer-review

15 Citations (Scopus)


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.
Original languageEnglish
Pages (from-to)10230-10234
Number of pages5
Issue number49
Publication statusPublished - 27 Sep 2009

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