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Enantioselective Syntheses of Authentic Sclerophytin A, Sclerophytin B, and Cladiell-11-ene-3,6,7-triol

Gallou, Fabrice and MacMillan, David W. C. and Overman, Larry E. and Paquette, Leo A. and Pennington, Lewis D. and Yang, Jiong (2001) Enantioselective Syntheses of Authentic Sclerophytin A, Sclerophytin B, and Cladiell-11-ene-3,6,7-triol. Organic Letters, 3 (1). pp. 135-137. ISSN 1523-7060. https://resolver.caltech.edu/CaltechAUTHORS:20170808-072534739

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Abstract

Two distinctively different total syntheses of natural sclerophytin A in its revised structural formulation are reported. The first proceeds from (S)-carvone via a cladiellene triol and involves photoisomerization of the double bond. The second route makes use of (5S)-5-(d-menthyloxy)-2(5H)-furanone, which is subjected to cycloaddition, Claisen ring expansion, and regiocontrolled dihydroxylation tactics.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ol000345mDOIArticle
http://pubs.acs.org/doi/abs/10.1021/ol000345mPublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/ol000345mPublisherSupporting Information
Additional Information:© 2001 American Chemical Society. Received 13 November 2000. Published online 6 December 2000. Published in print 1 January 2001. The research at Irvine was financed by NIH Grant NS-12389 and a Pharmacia Graduate Fellowship in Synthetic Organic Chemistry to L.D.P. Financial support at Ohio State was provided by Eli Lilly and Company. The authors thank Professor Kenneth Euler (University of Houston) for kindly providing samples of natural sclerophytins A and B and Professor Yasuto Uchio (Kagoshima University) for making authentic cladiell-11-ene-3,6,7-triol available to us.
Funders:
Funding AgencyGrant Number
NIHNS-12389
PharmaciaUNSPECIFIED
Eli Lilly and CompanyUNSPECIFIED
Issue or Number:1
Record Number:CaltechAUTHORS:20170808-072534739
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170808-072534739
Official Citation:Enantioselective Syntheses of Authentic Sclerophytin A, Sclerophytin B, and Cladiell-11-ene-3,6,7-triol Fabrice Gallou, David W. C. MacMillan, Larry E. Overman, Leo A. Paquette, Lewis D. Pennington, and Jiong Yang Organic Letters 2001 3 (1), 135-137 DOI: 10.1021/ol000345m
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:79901
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:09 Aug 2017 20:43
Last Modified:03 Oct 2019 18:25

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