Scalable, stereocontrolled total syntheses of (±)-axinellamines A and B

J Am Chem Soc. 2011 Sep 7;133(35):13922-5. doi: 10.1021/ja206191g. Epub 2011 Aug 16.

Abstract

The development of a simple, efficient, scalable, and stereocontrolled synthesis of a common intermediate en route to the axinellamines, massadines, and palau'amine is reported. This completely new route was utilized to prepare the axinellamines on a gram scale. In a more general sense, three distinct and enabling methodological advances were made during these studies: (1) an ethylene glycol-assisted Pauson-Khand cycloaddition reaction, (2) a Zn/In-mediated Barbier-type reaction, and (3) a TfNH(2)-assisted chlorination-spirocyclization.

Publication types

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

MeSH terms

  • Chemistry Techniques, Synthetic / economics
  • Chemistry Techniques, Synthetic / methods*
  • Guanidines / chemical synthesis
  • Imidazoles / chemical synthesis*
  • Pyrroles / chemical synthesis*
  • Spiro Compounds / chemical synthesis
  • Stereoisomerism

Substances

  • Guanidines
  • Imidazoles
  • Pyrroles
  • Spiro Compounds
  • axinellamine
  • massadine
  • palau'amine