An intramolecular furan-diene diels-alder approach to 11-oxo 10α-steroids

Sandra Claeys; Dirk Van Haver; Pierre J. De Clercq; Marco Milanesio; Davide Viterbo

doi:10.1002/1099-0690(200203)2002:6<1051::aid-ejoc1051>3.0.co;2-%23

An intramolecular furan-diene diels-alder approach to 11-oxo 10α-steroids

Sandra Claeys, Dirk Van Haver, Pierre J. De Clercq, Marco Milanesio, Davide Viterbo

Risultato della ricerca: Contributo su rivista › Articolo in rivista › peer review

Abstract

The intramolecular cycloaddition of 14, with dimethylaluminium chloride as a catalyst and under kinetic control, yielded the exo adduct 19a. Opening of the oxygen bridge in the reduced adduct 20 gave intermediate 21. Oxidation of the latter made it possible to introduce the methyl group at C-10, which exclusively afforded 23, with the unnatural configuration. Further conversion resulted in the formation of D-homo-10-epi-adrenosterone (25).

Lingua originale	Inglese
pagine (da-a)	1051-1062
Numero di pagine	12
Rivista	European Journal of Organic Chemistry
Numero di pubblicazione	6
DOI	https://doi.org/10.1002/1099-0690(200203)2002:6<1051::aid-ejoc1051>3.0.co;2-%23
Stato di pubblicazione	Pubblicato - 2002
Pubblicato esternamente	Sì

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10.1002/1099-0690(200203)2002:6<1051::aid-ejoc1051>3.0.co;2-%23

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title = "An intramolecular furan-diene diels-alder approach to 11-oxo 10α-steroids",

abstract = "The intramolecular cycloaddition of 14, with dimethylaluminium chloride as a catalyst and under kinetic control, yielded the exo adduct 19a. Opening of the oxygen bridge in the reduced adduct 20 gave intermediate 21. Oxidation of the latter made it possible to introduce the methyl group at C-10, which exclusively afforded 23, with the unnatural configuration. Further conversion resulted in the formation of D-homo-10-epi-adrenosterone (25).",

keywords = "Cycloadditions, Steroid, Synthetic methods",

author = "Sandra Claeys and {Van Haver}, Dirk and {De Clercq}, {Pierre J.} and Marco Milanesio and Davide Viterbo",

year = "2002",

doi = "10.1002/1099-0690(200203)2002:6<1051::aid-ejoc1051>3.0.co;2-%23",

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AU - Milanesio, Marco

AU - Viterbo, Davide

PY - 2002

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AB - The intramolecular cycloaddition of 14, with dimethylaluminium chloride as a catalyst and under kinetic control, yielded the exo adduct 19a. Opening of the oxygen bridge in the reduced adduct 20 gave intermediate 21. Oxidation of the latter made it possible to introduce the methyl group at C-10, which exclusively afforded 23, with the unnatural configuration. Further conversion resulted in the formation of D-homo-10-epi-adrenosterone (25).

KW - Cycloadditions

KW - Steroid

KW - Synthetic methods

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JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

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ER -

An intramolecular furan-diene diels-alder approach to 11-oxo 10α-steroids

Abstract

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