An enantioselective version of the AB+B→ABCD-type steroid total synthesis

Autor:	Markus Bauch, Michael del Grosso, Jan W. Bats, Gerd Dürner, Astrid Bucher, Wolfgang Döring, Gerhard Quinkert
Rok vydání:	1992
Předmět:	Diene Stereochemistry Organic Chemistry Enantioselective synthesis Total synthesis Biochemistry Adduct chemistry.chemical_compound Acid catalysis chemistry Drug Discovery Lewis acids and bases Enone Deoxygenation
Zdroj:	Tetrahedron Letters. 33:3617-3620
ISSN:	0040-4039
DOI:	10.1016/s0040-4039(00)92517-6
Popis:	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 recrystalization affords 5b. The latter compound can easily be converted via Torgov's pentaenone 6a into estrogens or progestogens.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::be3f6b3743b60973286846c2ff0b24ed https://doi.org/10.1016/s0040-4039(00)92517-6 Zobrazit plný text záznamu