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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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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Abstract 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.
AbstractList 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.
Author NICKSON, TE
SINDELAR, RD
VACCA, JP
LANSBURY, PT
MESSINGER, JM
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LANSBURY, PT (WOS:A1982PR93100006) 1982; 38
ROBERTS, MR (WOS:A1979HW19000032) 1979; 101
LANSBURY PT (WOS:A1987L250000011.11) 1981
PETTIT, GR (WOS:A1978ER32700015) 1978; 43
EINCK, JJ (WOS:A1978FA09100041) 1978; 100
LANSBURY, PT (WOS:A1980KS37400004) 1980; 36
LANSBURY, PT (WOS:A1982NU20500006) 1982; 23
LANSBURY, PT (WOS:A1982NU20500005) 1982; 23
VONDREELE, RB (WOS:A1975AP07200039) 1975; 97
HERZ, W (WOS:A1970I011100023) 1970; 35
HEATHCOCK CH (WOS:A1987L250000011.4) 1983; 5
HEATHCOCK, CH (WOS:A1982PN67000040) 1982; 104
WOODWARD, RB (WOS:A1958WB37600053) 1958; 80
PATAKI, J (WOS:A1972M858700014) 1972; 37
MESSINGER JM (WOS:A1987L250000011.12) 1986
NICKSON TE (WOS:A1987L250000011.13) 1982
VACCA JP (WOS:A1987L250000011.18) 1983
FISCHER NH (WOS:A1987L250000011.2) 1979; 38
HERZ, W (WOS:A19667769600021) 1966; 22
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Snippet A synthetic route to highly-oxygenated pseudoguaianolide intermediates has been developed. The functional groups on the seven-membered rings were introduced...
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SubjectTerms Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Title TOTAL SYNTHESIS OF PSEUDOGUAIANOLIDES .5. STEREOCONTROLLED APPROACHES TO THE FASTIGILINS - (+/-)-2,3-DIHYDROFASTIGILIN-C
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