Synthesis of the N-((1E)-alkenyl)-(2Z,4Z)-heptadienamide side chain of salicylihalamide A and apicularens A and B

Org Lett. 2000 Feb 10;2(3):407-8. doi: 10.1021/ol991388+.

Abstract

[reaction: see text] The unstable N-((1E)-alkenyl)-(2Z,4Z)-heptadienamide side chain of salicylihalamide A (1) and apicularens A and B (3 and 4) has been prepared in one pot by the addition of (1Z,3Z)-hexadienylcuprate, prepared in situ from EtLi, CuBr.SMe2, and acetylene, to a (1 E)-alkenyl isocyanate.

Publication types

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

MeSH terms

  • Animals
  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry*
  • Antibiotics, Antineoplastic / chemical synthesis
  • Antibiotics, Antineoplastic / chemistry*
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / isolation & purification
  • Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
  • Bridged Bicyclo Compounds, Heterocyclic / chemistry*
  • Macrolides*
  • Mycobacterium / chemistry
  • Porifera / chemistry

Substances

  • Anti-Bacterial Agents
  • Antibiotics, Antineoplastic
  • Antineoplastic Agents
  • Bridged Bicyclo Compounds, Heterocyclic
  • Macrolides
  • apicularen A
  • apicularen B
  • salicylihalamide A