TOTAL SYNTHESIS OF PSEUDOGUAIANOLIDES .5. STEREOCONTROLLED APPROACHES TO THE FASTIGILINS - (+/-)-2,3-DIHYDROFASTIGILIN-C

A synthetic route to highly-oxygenated pseudoguaianolide intermediates has been developed. The functional groups on the seven-membered rings were introduced stereoselectively at all seven chiral centers. In addition, regioselective esterification at C-6 hydroxyl groups, in the presence of a C-9 hydr...

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Bibliographic Details
Published inTetrahedron Vol. 43; no. 23; pp. 5583 - 5592
Main Authors LANSBURY, PT, NICKSON, TE, VACCA, JP, SINDELAR, RD, MESSINGER, JM
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 01.01.1987
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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Summary:A synthetic route to highly-oxygenated pseudoguaianolide intermediates has been developed. The functional groups on the seven-membered rings were introduced stereoselectively at all seven chiral centers. In addition, regioselective esterification at C-6 hydroxyl groups, in the presence of a C-9 hydroxyl site, was achieved.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(01)87739-5