Asymmetric aldol reaction of thiazole-carbaldehydes: Regio- And stereoselective synthesis of tubuvalin analogues

Sushovan Paladhi, Joydeb Das, Mousumi Samanta, Jyotirmayee Dash

Research output: Contribution to journalArticlepeer-review

10 Scopus citations

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.

Original languageEnglish
Pages (from-to)3370-3376
Number of pages7
JournalAdvanced Synthesis and Catalysis
Volume356
Issue number16
DOIs
StatePublished - 3 Nov 2014
Externally publishedYes

Keywords

  • Asymmetric catalysis
  • Green chemistry
  • Reductive amination
  • Regioselectivity
  • Tubulysins

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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