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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Published in | Tetrahedron letters Vol. 33; no. 25; pp. 3617 - 3620 |
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Main Authors | , , , , , , |
Format | Journal Article |
Language | English |
Published |
OXFORD
Elsevier
16.06.1992
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Subjects | |
Online Access | Get more information |
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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. |
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ISSN: | 0040-4039 |
DOI: | 10.1016/S0040-4039(00)92517-6 |