Rhodium-catalyzed reductive cyclization of 1,6-enynes and stereoselective synthesis of the putative structure of lucentamycin A and its stereoisomers

Young Jin Ham, Hana Yu, Nam Doo Kim, Jung Mi Hah, Khalid B. Selim, Hwan Geun Choi, Taebo Sim

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

A Rh-catalyzed diastereoselective reductive cyclization, mediated by hydrogen, of optically active 1,6-enynes using chiral BINAP was successfully applied to the total synthesis of four stereoisomers of the proposed structure of lucentamycin A. In order to synthesize two of these four stereoisomers, we successfully constructed chiral proline derivatives bearing cis-carbon substituents at C2 and C3 positions based on Krische's methodology, which has very rarely been reported. Anti-proliferative activities on HCT-116 cell line and NMR data of these four stereoisomers were compared with those of naturally occurring lucentamycine A. The results show that the proposed structure of lucentamycin A needs revision.

Original languageEnglish
Pages (from-to)1918-1925
Number of pages8
JournalTetrahedron
Volume68
Issue number7
DOIs
Publication statusPublished - 2012 Feb 18

Keywords

  • 1,6-Enynes
  • Lucentamycin A
  • Natural product
  • Reductive cyclization
  • Structure revision

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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