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

Access to Document

10.1016/S0040-4039(01)80565-7

Cite this

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 et al.

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

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

@article{64a1216d14f44d9d96836a94a82a8901,

title = "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 = "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.",

author = "Takashi Takahashi and Katsuya Shimizu and Takayuki Doi and Jiro Tsuji and Keiji Yamamoto",

year = "1989",

doi = "10.1016/S0040-4039(01)80565-7",

language = "English",

volume = "30",

pages = "4999--5002",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "37",

}

TY - JOUR

T1 - 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

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.

UR - http://www.scopus.com/inward/record.url?scp=0037882451&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0037882451&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(01)80565-7

DO - 10.1016/S0040-4039(01)80565-7

M3 - Article

AN - SCOPUS:0037882451

VL - 30

SP - 4999

EP - 5002

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 37

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

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this