An Efficient Stereoselective Synthesis of Stypodiol and Epistypodiol

An Efficient Stereoselective Synthesis of Stypodiol and Epistypodiol

An efficient synthesis of stypodiol (1) and its epimer at C-14, epistypodiol (2), was accomplished starting from (S)-(+)-carvone (7). The synthesis of both epimeric compounds proceeds through common intermediates using an IMDA reaction, a sonochemical Barbier reaction, and an acid-catalyzed quinol−t...

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Veröffentlicht in:Journal of organic chemistry 1998-07, Vol.63 (15), p.5100-5106
Hauptverfasser: Abad, Antonio, Agulló, Consuelo, Arnó, Manuel, Cuñat, Ana C, Meseguer, Benjamín, Zaragozá, Ramón J
Format: Artikel
Sprache:eng
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Zusammenfassung:An efficient synthesis of stypodiol (1) and its epimer at C-14, epistypodiol (2), was accomplished starting from (S)-(+)-carvone (7). The synthesis of both epimeric compounds proceeds through common intermediates using an IMDA reaction, a sonochemical Barbier reaction, and an acid-catalyzed quinol−tertiary alcohol cyclization as key synthetic steps.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo980311g