Total synthesis of (+)-laurencin: an asymmetric alkylation-ring-closing metathesis approach to medium ring ethers

Org Lett. 1999 Dec 16;1(12):2029-32. doi: 10.1021/ol991201e.

Abstract

[formula: see text] The enantioselective total synthesis of (+)-laurencin 1 is achieved in 18 steps from (S)-(+)-4-benzyl-3-benzyloxyacetyl-2-oxazolidinone. The key steps in this synthesis are an asymmetric glycolate alkylation leading to acyl oxazolidinone 2 and a subsequent ring-closing olefin metathesis to construct the oxocene core of 1. The approach to medium ring ethers utilized in this synthesis provides a general and efficient route to the cyclic core of other marine natural products.

Publication types

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

MeSH terms

  • Aldehydes
  • Alkylation
  • Ethers
  • Ethers, Cyclic / chemical synthesis*
  • Magnetic Resonance Spectroscopy
  • Oxazoles / chemical synthesis*
  • Oxazolidinones*
  • Oxocins*
  • Spectrophotometry, Infrared
  • Stereoisomerism

Substances

  • 4-benzyl-3-benzyloxyacetyl-2-oxazolidinone
  • Aldehydes
  • Ethers
  • Ethers, Cyclic
  • Oxazoles
  • Oxazolidinones
  • Oxocins
  • laurencin