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Published January 11, 2001 | Supplemental Material
Journal Article Open

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


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.

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.

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