Enantioselective formal synthesis of (-)-englerin A via a Rh-catalyzed [4 + 3] cycloaddition reaction

Org Lett. 2010 Aug 20;12(16):3708-11. doi: 10.1021/ol1015652.

Abstract

An enantioselective formal synthesis of (-)-englerin A (1) is reported. Key to the strategy is a Rh-catalyzed [4 + 3] cycloaddition reaction between furan 10 and diazo ester 11 that, following an intramolecular aldol condensation, produces the tricyclic scaffold of englerin. This strategy also provides a rapid, efficient, and stereoselective access to the biologically significant core motif of the guaiane sesquiterpenes.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemical synthesis*
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Catalysis
  • Cyclization
  • Furans / chemistry*
  • Molecular Structure
  • Rhodium / chemistry*
  • Sesquiterpenes, Guaiane / chemical synthesis*
  • Sesquiterpenes, Guaiane / chemistry
  • Sesquiterpenes, Guaiane / pharmacology
  • Stereoisomerism

Substances

  • Antineoplastic Agents, Phytogenic
  • Furans
  • Sesquiterpenes, Guaiane
  • englerin A
  • englerin B
  • Rhodium