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Published February 8, 2006 | Version Supplemental Material
Journal Article Open

Total Synthesis of (±)-Welwitindolinone A Isonitrile

Creators

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.

Additional Information

© 2006 American Chemical Society. Received November 9, 2005; Publication Date (Web): January 11, 2006. Financial support was provided by Bristol-Myers Squibb, Yamanouchi, Merck, Amgen, Pfizer, and the NIH (Grant No. 1 R01 CA/GM 93591-01A). S.E.R. thanks Bristol-Myers Squibb for a graduate student fellowship. J.M.R. was the recipient of a NIH postdoctoral fellowship. In addition, we acknowledge and thank C.D. Incarvito for X-ray crystallographic analysis.

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Supplemental Material - ja057640ssi20060105_023252.pdf

Supplemental Material - ja057640ssi20060105_023331.pdf

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Additional details

Identifiers

Eprint ID
75605
DOI
10.1021/ja057640s
Resolver ID
CaltechAUTHORS:20170331-145008719

Funding

Bristol-Myers Squibb
Yamanouchi
Merck
Amgen
Pfizer
NIH
1 R01 CA/GM 93591-01A
NIH Postdoctoral Fellowship

Dates

Created
2017-04-03
Created from EPrint's datestamp field
Updated
2021-11-15
Created from EPrint's last_modified field