Facile asymmetric construction of a functionalized dodecahydrobenz[a]indolo[3,2-h]quinolizine template |
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Authors: | Steven M. Allin Liam J. Duffy Philip C. Bulman Page Basu Saha |
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Affiliation: | a School of Physical and Geographical Sciences, Keele University, ST5 5BG, UK b Department of Chemistry, Loughborough University, LE11 3TU, UK c School of Chemical Sciences and Pharmacy, University of East Anglia, NR4 7TJ, UK d Department of Chemical Engineering, Loughborough University, LE11 3TU, UK |
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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. |
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Keywords: | Natural product Heterocyclic Acyliminium Asymmetric Cyclization |
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