Published January 11, 2001
| Version Supplemental Material
Journal Article
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Facile Entry to the Tetracyclic 5-7-6-3 Tigliane Ring System
Abstract
A tandem anionic 5-exo-dig cyclization/Claisen rearrangement sequence was used to effect a facile, "one-pot" conversion of an appropriately substituted 4-alkyn-1-ol to the tetracyclic carbon core structure of phorbol. The synthesis was conducted using readily available nonracemic starting materials to provide the target structure as a single enantiomer in high chemical yield.
Additional Information
© 2001 American Chemical Society. Received November 3, 2000. Publication Date (Web): December 15, 2000. This work was supported by grants from the donors of the Petroleum Research Fund, administered by the American Chemical Society, the Research Corporation (Cottrell College Science Award), and the National Institutes of Health (GM60972-01). S.E.R. and M.A.F. acknowledge Pfizer, Inc., for Summer Fellowships (Pfizer Summer Undergraduate Fellowship and PREPARE programs). We are also grateful to Dr. Walt Massefski of Pfizer Central Research, Groton, CT, for performing a complete NMR analysis of compound 16.Attached Files
Supplemental Material - ol006823a_s1.pdf
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ol006823a_s1.pdf
Additional details
Identifiers
- Eprint ID
- 75656
- DOI
- 10.1021/ol006823a
- Resolver ID
- CaltechAUTHORS:20170403-155648365
Funding
- American Chemical Society Petroleum Research Fund
- Research Corporation
- NIH
- GM60972-01
- Pfizer, Inc.
Dates
- 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