Total synthesis of (+/-)-welwitindolinone a isonitrile

Sarah E Reisman; Joseph M Ready; Atsushi Hasuoka; Catherine J Smith; John L Wood

doi:10.1021/ja057640s

Total synthesis of (+/-)-welwitindolinone a isonitrile

J Am Chem Soc. 2006 Feb 8;128(5):1448-9. doi: 10.1021/ja057640s.

Authors

Sarah E Reisman¹, Joseph M Ready, Atsushi Hasuoka, Catherine J Smith, John L Wood

Affiliation

¹ Sterling Chemistry Laboratory, Department of Chemistry, Yale University, New Haven, Connecticut 06520-8107, USA.

PMID: 16448105
DOI: 10.1021/ja057640s

Abstract

A highly stereoselective total synthesis of the alkaloid natural product welwitindolinone A isonitrile has been completed. The synthesis utilizes a chloronium ion mediated semi-pinacol rearrangement to simultaneously install the C10 quaternary center and neopentyl chlorine and a novel anionic cyclization to construct the spiro-oxindole with complete stereocontrol.

Publication types

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

MeSH terms

Cyanobacteria / chemistry
Indole Alkaloids
Indoles / chemical synthesis*
Indoles / chemistry
Nitriles / chemical synthesis*
Nitriles / chemistry

Substances

Indole Alkaloids
Indoles
Nitriles
welwitindolinone A

Abstract

Publication types

MeSH terms

Substances

Grants and funding