Synthesis of the diazonamide A macrocyclic core via a Dieckmann-type cyclization

Org Lett. 2001 Aug 9;3(16):2451-4. doi: 10.1021/ol016097r.

Abstract

[reaction: see text] Suzuki coupling of 18 and 30 affords 9 as an interconverting mixture of two atropisomers. Treatment with LDA at -23 degrees C affords the macrocyclic ketone 8 in 57% yield.

Publication types

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

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Cyclization
  • Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
  • Heterocyclic Compounds, 4 or More Rings / chemistry
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Marine Toxins / chemical synthesis*
  • Marine Toxins / chemistry
  • Oxazoles / chemical synthesis*
  • Oxazoles / chemistry

Substances

  • Antineoplastic Agents
  • Heterocyclic Compounds, 4 or More Rings
  • Indicators and Reagents
  • Marine Toxins
  • Oxazoles
  • diazonamide A