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Facile Entry to the Tetracyclic 5-7-6-3 Tigliane Ring System

Ovaska, Timo V. and Reisman, Sarah E. and Flynn, Meghan A. (2001) Facile Entry to the Tetracyclic 5-7-6-3 Tigliane Ring System. Organic Letters, 3 (1). pp. 115-117. ISSN 1523-7060. https://resolver.caltech.edu/CaltechAUTHORS:20170403-155648365

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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.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ol006823aDOIArticle
http://pubs.acs.org/doi/abs/10.1021/ol006823aPublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/ol006823aPublisherSupporting Information
ORCID:
AuthorORCID
Reisman, Sarah E.0000-0001-8244-9300
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.
Funders:
Funding AgencyGrant Number
American Chemical Society Petroleum Research FundUNSPECIFIED
Research CorporationUNSPECIFIED
NIHGM60972-01
Pfizer, Inc.UNSPECIFIED
Issue or Number:1
Record Number:CaltechAUTHORS:20170403-155648365
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170403-155648365
Official Citation:Facile Entry to the Tetracyclic 5-7-6-3 Tigliane Ring System Timo V. Ovaska, Sarah E. Reisman, and Meghan A. Flynn Organic Letters 2001 3 (1), 115-117 DOI: 10.1021/ol006823a
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:75656
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:03 Apr 2017 23:33
Last Modified:03 Oct 2019 16:52

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