Efficient approach to the oppolzer-kametani intermediate for estrone methyl ether using the conjugate addition-enolate methylation of the cyclopentenone containing an α-appended benzocyclobutane moiety

Takashi Takahashi; Katsuya Shimizu; Takayuki Doi; Jiro Tsuji; Keiji Yamamoto

doi:10.1016/S0040-4039(01)80565-7

Efficient approach to the oppolzer-kametani intermediate for estrone methyl ether using the conjugate addition-enolate methylation of the cyclopentenone containing an α-appended benzocyclobutane moiety

Takashi Takahashi, Katsuya Shimizu, Takayuki Doi, Jiro Tsuji, Keiji Yamamoto

Research output: Contribution to journal › Article › peer-review

14 Citations (Scopus)

Abstract

Simple synthesis of (±)-estrone methyl ether by the conjugate addition-enolate methylation of the 2-alkylcyclopentenone followed by the intramolecular Diels-Alder reaction of the o-quinodimethane, and discussions for the diastereoselectivity in the enolatemethylation based on the MM2 transition structure model are presented.

Original language	English
Pages (from-to)	4999-5002
Number of pages	4
Journal	Tetrahedron Letters
Volume	30
Issue number	37
DOIs	https://doi.org/10.1016/S0040-4039(01)80565-7
Publication status	Published - 1989
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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Efficient approach to the oppolzer-kametani intermediate for estrone methyl ether using the conjugate addition-enolate methylation of the cyclopentenone containing an α-appended benzocyclobutane moiety. / Takahashi, Takashi; Shimizu, Katsuya; Doi, Takayuki; Tsuji, Jiro; Yamamoto, Keiji.

In: Tetrahedron Letters, Vol. 30, No. 37, 1989, p. 4999-5002.

Research output: Contribution to journal › Article › peer-review

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abstract = "Simple synthesis of (±)-estrone methyl ether by the conjugate addition-enolate methylation of the 2-alkylcyclopentenone followed by the intramolecular Diels-Alder reaction of the o-quinodimethane, and discussions for the diastereoselectivity in the enolatemethylation based on the MM2 transition structure model are presented.",

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AU - Takahashi, Takashi

AU - Shimizu, Katsuya

AU - Doi, Takayuki

AU - Tsuji, Jiro

AU - Yamamoto, Keiji

PY - 1989

Y1 - 1989

N2 - Simple synthesis of (±)-estrone methyl ether by the conjugate addition-enolate methylation of the 2-alkylcyclopentenone followed by the intramolecular Diels-Alder reaction of the o-quinodimethane, and discussions for the diastereoselectivity in the enolatemethylation based on the MM2 transition structure model are presented.

AB - Simple synthesis of (±)-estrone methyl ether by the conjugate addition-enolate methylation of the 2-alkylcyclopentenone followed by the intramolecular Diels-Alder reaction of the o-quinodimethane, and discussions for the diastereoselectivity in the enolatemethylation based on the MM2 transition structure model are presented.

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ER -

Efficient approach to the oppolzer-kametani intermediate for estrone methyl ether using the conjugate addition-enolate methylation of the cyclopentenone containing an α-appended benzocyclobutane moiety

Abstract

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