Synthesis of an oxazoline analogue of apratoxin A

Org Lett. 2003 Sep 18;5(19):3503-6. doi: 10.1021/ol035332y.

Abstract

[structure: see text] Michael addition of Me(2)Cu(CN)Li(2) to alpha,beta-unsaturated lactone 7 derived from beta-hydroxyl ketone 5 provides lactone 8, which is converted to alcohol 11 using Oppolzer's methodology as the key step. Connection of 11 with the l-proline moiety and subsequent installation of an oxazoline ring affords 16, which is coupled with tripeptide 21; subsequent macrocyclization then furnishes 4, an oxazoline analogue of apratoxin A.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Cyclization
  • Cytotoxins / chemical synthesis*
  • Depsipeptides*
  • Ketones / chemistry
  • Lactones / chemical synthesis
  • Models, Chemical
  • Molecular Structure
  • Oxazoles / chemical synthesis*
  • Peptides / chemistry
  • Peptides, Cyclic / chemical synthesis*
  • Proline / chemistry
  • Stereoisomerism
  • Structure-Activity Relationship
  • Thiazoles / chemistry

Substances

  • Antineoplastic Agents
  • Cytotoxins
  • Depsipeptides
  • Ketones
  • Lactones
  • Oxazoles
  • Peptides
  • Peptides, Cyclic
  • Thiazoles
  • apratoxin A
  • Proline