Enantioselective synthesis of the C1-C6 and C7-C23 fragments of the proposed structure of iriomoteolide 1a

Org Lett. 2012 May 4;14(9):2366-9. doi: 10.1021/ol300785c. Epub 2012 Apr 18.

Abstract

Synthesis of the C1-C6 and C7-C23 fragments of the proposed structure of iriomoteolide 1a has been accomplished. Key steps include a cross metathesis to form the C15-C16 E olefin and a chelation controlled Grignard addition to form the tertiary alcohol at C14. Notably, 7 of the 9 stereocenters of the proposed structure have been set using various aldol reactions employing metallo enolates of thiazolidinethiones.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Aldehydes / chemistry
  • Macrolides / chemical synthesis*
  • Macrolides / chemistry
  • Molecular Structure
  • Stereoisomerism
  • Thiazolidines / chemistry*

Substances

  • Aldehydes
  • Macrolides
  • Thiazolidines
  • iriomoteolide-1a
  • thiazoline-2-thione
  • 3-hydroxybutanal