Efficient construction of the securine A carbon skeleton

Proc Natl Acad Sci U S A. 2004 Aug 17;101(33):12054-7. doi: 10.1073/pnas.0402274101. Epub 2004 Jul 27.

Abstract

Securamine A is a structurally intriguing alkaloid possessing a pyrroloindole core joined via a modified isoprene subunit to a functionalized imidazole ring. Recent synthetic efforts in this laboratory have resulted in the efficient construction of key lactone 36, which undergoes tandem azide reduction/ring expansion to macrolactam 37. Macrolactam 37 possesses the complete macrocyclic core of securamine A.

Publication types

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

MeSH terms

  • Animals
  • Biological Products / chemical synthesis
  • Biological Products / chemistry
  • Bryozoa / chemistry
  • Chemistry, Organic / methods
  • Indole Alkaloids / chemical synthesis*
  • Indole Alkaloids / chemistry*
  • Molecular Structure

Substances

  • Biological Products
  • Indole Alkaloids