Published February 8, 2006
| Supplemental Material
Journal Article
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Total Synthesis of (±)-Welwitindolinone A Isonitrile
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.Attached Files
Supplemental Material - ja057640ssi20051109_013604.cif
Supplemental Material - ja057640ssi20051109_013625.cif
Supplemental Material - ja057640ssi20060105_023252.pdf
Supplemental Material - ja057640ssi20060105_023331.pdf
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ja057640ssi20060105_023252.pdf
Additional details
- Eprint ID
- 75605
- DOI
- 10.1021/ja057640s
- Resolver ID
- CaltechAUTHORS:20170331-145008719
- Bristol-Myers Squibb
- Yamanouchi
- Merck
- Amgen
- Pfizer
- 1 R01 CA/GM 93591-01A
- NIH
- NIH Postdoctoral Fellowship
- Created
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2017-04-03Created from EPrint's datestamp field
- Updated
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2021-11-15Created from EPrint's last_modified field