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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Bibliographic Details
Published inJournal of organic chemistry Vol. 63; no. 15; pp. 5100 - 5106
Main Authors Abad, Antonio, Agulló, Consuelo, Arnó, Manuel, Cuñat, Ana C, Meseguer, Benjamín, Zaragozá, Ramón J
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 24.07.1998
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
METABOLITES
SEA-URCHIN EMBRYOS
(-)-STYPOLDIONE
ABSOLUTE-CONFIGURATION
STYPOLDIONE
ORGANIC HALIDES
DITERPENOID TOTAL SYNTHESIS
SEAWEED
MARINE NATURAL-PRODUCTS
STYPOPODIUM-ZONALE
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Summary: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.
Bibliography:ark:/67375/TPS-T5PHQ64Q-Z
istex:FB1CA18925A9A1244C9FA8C18E2DA3BF4AB45614
ISSN:0022-3263
1520-6904
DOI:10.1021/jo980311g