A concise enantioselective synthesis of the AB ring system of the manzamine alkaloids by ring-closing enyne metathesis

The AB ring system found in the manzamine A and related alkaloids has been prepared from (−)-quinine by a short enantioselective route. The key step in the sequence is a ruthenium-catalysed ring-closing enyne metathesis re action which delivers a bicyclic diene in good yield. The functionality requi...

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Bibliographic Details
Published in:Tetrahedron letters 2001-04, Vol.42 (18), p.3235-3238
Main Authors: Clark, J.Stephen, Townsend, Robert J, Blake, Alexander J, Teat, Simon J, Johns, Amanda
Format: Article
Language:English
Subjects:
alkaloids
enyne
manzamine
metathesis
ring-closing
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Summary:The AB ring system found in the manzamine A and related alkaloids has been prepared from (−)-quinine by a short enantioselective route. The key step in the sequence is a ruthenium-catalysed ring-closing enyne metathesis re action which delivers a bicyclic diene in good yield. The functionality required for further elaboration of the AB system has been installed by sequential regioselective hydroboration and stereoselective catalytic aminohydroxylation. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(01)00404-X