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- Title
Asymmetric Aldol Reaction of Thiazole-Carbaldehydes: Regio- and Stereoselective Synthesis of Tubuvalin Analogues.
- Authors
Paladhi, Sushovan; Das, Joydeb; Samanta, Mousumi; Dash, Jyotirmayee
- Abstract
The first organocatalytic enantioselective approach to precursors of tubuvaline (pre-Tuv) is presented employing a prolinamide-catalyzed aldol reaction of easily accessible thiazole-carbaldehyde with methyl isopropyl ketone 'on water' in excellent yield as well as regio- and enantioselectivities. The analogues of pre-Tuv were achieved using an L-proline-catalyzed direct asymmetric aldol reaction of substituted thiazole-carbaldehydes with acetone. A direct and flexible approach to the tubavaline (Tuv) core of tubusylins has been established employing the reductive amination of the pre-Tuv species. The key aldol reaction should greatly expand the potential of this strategy to the synthesis of natural product tubulysins and a range of analogues.
- Subjects
STEREOSELECTIVE reactions; ENANTIOSELECTIVE catalysis; ACETONE; CHEMICAL synthesis; AMINATION; REGIOSELECTIVITY (Chemistry)
- Publication
Advanced Synthesis & Catalysis, 2014, Vol 356, Issue 16, p3370
- ISSN
1615-4150
- Publication type
Article
- DOI
10.1002/adsc.201400640