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. http://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:

URL	URL Type	Description
http://dx.doi.org/10.1021/ol006823a	DOI	Article
http://pubs.acs.org/doi/abs/10.1021/ol006823a	Publisher	Article
http://pubs.acs.org/doi/suppl/10.1021/ol006823a	Publisher	Supporting Information

ORCID:

Author	ORCID
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 Agency	Grant Number
American Chemical Society Petroleum Research Fund	UNSPECIFIED
Research Corporation	UNSPECIFIED
NIH	GM60972-01
Pfizer, Inc.	UNSPECIFIED

Record Number:

CaltechAUTHORS:20170403-155648365

Persistent URL:

http://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

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ID Code:

75656

Collection:

CaltechAUTHORS

Deposited By:

Tony Diaz

Deposited On:

03 Apr 2017 23:33

Last Modified:

03 Apr 2017 23:33

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