Efficient asymmetric synthesis of (+)-SCH 351448

Org Lett. 2005 Aug 18;7(17):3809-12. doi: 10.1021/ol0515006.

Abstract

An efficient and stereocontrolled total synthesis of (+)-SCH 351448, a novel activator of low-density lipoprotein receptor promoter, has been achieved with a longest linear sequence of 21 steps. Key steps include applications of the recently developed asymmetric allyl- and crotylsilane reagents and a new protodesilylative version of the tandem silylformylation/allylsilylation reaction, which provides an efficient synthesis of 1,5-syn-diols. [reaction: see text]

Publication types

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

MeSH terms

  • Alcohols / chemical synthesis
  • Catalysis
  • Lactones / chemical synthesis*
  • Lactones / chemistry
  • Molecular Structure
  • Receptors, LDL / agonists*
  • Receptors, LDL / genetics
  • Silanes / chemistry*
  • Stereoisomerism

Substances

  • Alcohols
  • Lactones
  • Receptors, LDL
  • SCH 351448
  • Silanes