Tetrahedron Letters p. 3617 - 3620 (1992)
Update date:2022-07-30
Topics:
Quinkert, Gerhard
Grosso, Michael del
Bucher, Astrid
Bauch, Markus
Doering, Wolfgang
et al.
Diene 1 and dienophile 4a in a Diels/Alder reaction mediated by a chiral ligand-modified Lewis acid enantioselectively furnish adduct 5a (chem. yield: 64percent; e.e: 73percent), 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. Key Words: stereoid total synthesis, enantioselective Lewis acid-mediated Diels/Alder reaction
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