AN ENANTIOSELECTIVE VERSION OF THE AB+D-]ABCD- TYPE STEROID TOTAL SYNTHESIS

Diene 1 and dienophile 4a in a Diels/Alder reaction mediated by a chiral ligand-modified Lewis acid enantioselectively furnish adduct 5a (chem. yield. 64%, e.e.: 73%), which after partial deoxygenation and final enantioselection by recrystallization affords 5b. The latter compound can easily be conv...

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Bibliographic Details
Published inTetrahedron letters Vol. 33; no. 25; pp. 3617 - 3620
Main Authors QUINKERT, G, DELGROSSO, M, BUCHER, A, BAUCH, M, DORING, W, BATS, JW, DURNER, G
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 16.06.1992
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
STEROID TOTAL SYNTHESIS
ENANTIOSELECTIVE LEWIS ACID-MEDIATED DIELS ALDER REACTION
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Summary:Diene 1 and dienophile 4a in a Diels/Alder reaction mediated by a chiral ligand-modified Lewis acid enantioselectively furnish adduct 5a (chem. yield. 64%, e.e.: 73%), which after partial deoxygenation and final enantioselection by recrystallization affords 5b. The latter compound can easily be converted via Torgov's pentaenone 6a into estrogens or progestogens.
ISSN:0040-4039
DOI:10.1016/S0040-4039(00)92517-6