Total synthesis of GEX1Q1, assignment of C-5 stereoconfiguration and evaluation of spliceosome inhibitory activity

Org Lett. 2014 Jun 6;16(11):3154-7. doi: 10.1021/ol501345d. Epub 2014 May 28.

Abstract

An enantioselective total synthesis of GEX1Q1 has been accomplished in a convergent manner. The C-5 asymmetric center has now been assigned through synthesis. GEX1Q1 displayed slightly better spliceosome inhibitory activity over its C-5 epimer. The salient features of this synthesis include an asymmetric hetero-Diels-Alder reaction to construct the tetrahydropyran ring and a Suzuki cross-coupling to assemble the key segments.

Publication types

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

MeSH terms

  • Cycloaddition Reaction
  • Fatty Alcohols / chemical synthesis*
  • Fatty Alcohols / chemistry
  • Fatty Alcohols / pharmacology
  • Macrolides
  • Molecular Structure
  • Pyrans / chemical synthesis*
  • Pyrans / chemistry
  • Pyrans / pharmacology
  • Spliceosomes
  • Stereoisomerism

Substances

  • Fatty Alcohols
  • Macrolides
  • Pyrans
  • herboxidiene