Novel stereoselective construction of a quaternary carbon: Application to synthesis of the cyclopentenedione moiety of madindolines

S. Hosokawa; K. Sekiguchi; M. Enemoto; S. Kobayashi

doi:10.1016/S0040-4039(00)00937-0

Novel stereoselective construction of a quaternary carbon: Application to synthesis of the cyclopentenedione moiety of madindolines

S. Hosokawa, K. Sekiguchi, M. Enemoto, S. Kobayashi^*

^*Corresponding author for this work

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

60 Citations (Scopus)

Abstract

Enantioselective synthesis of the cyclopentenedione moiety of madindolines was achieved. Stereoselective construction of a quaternary carbon was realized by alkylation of an enolate possessing chiral auxiliary. Cyclopentenedione was derived from a triketone precursor by intramolecular condensation. (C) 2000 Elsevier Science Ltd.

Original language	English
Pages (from-to)	6429-6433
Number of pages	5
Journal	Tetrahedron Letters
Volume	41
Issue number	33
DOIs	https://doi.org/10.1016/S0040-4039(00)00937-0
Publication status	Published - 2000 Aug 12
Externally published	Yes

Keywords

Alkylation
Cyclopentenedione
Madindoline
Quaternary carbon

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/S0040-4039(00)00937-0

Cite this

@article{827cdbf1cd8f4167b67d96384399abd0,

title = "Novel stereoselective construction of a quaternary carbon: Application to synthesis of the cyclopentenedione moiety of madindolines",

abstract = "Enantioselective synthesis of the cyclopentenedione moiety of madindolines was achieved. Stereoselective construction of a quaternary carbon was realized by alkylation of an enolate possessing chiral auxiliary. Cyclopentenedione was derived from a triketone precursor by intramolecular condensation. (C) 2000 Elsevier Science Ltd.",

keywords = "Alkylation, Cyclopentenedione, Madindoline, Quaternary carbon",

author = "S. Hosokawa and K. Sekiguchi and M. Enemoto and S. Kobayashi",

note = "Funding Information: We thank Prof. T. Sunazuka (Kitasato University) for helpful discussions. This work was supported in part by the Fujisawa Foundation (S.H.), Grant-in-Aid for Scientific Research from the Ministry of Education, Science, Sports, and Culture, Japan, and Shin-Etsu Chemical Co., Ltd.",

year = "2000",

month = aug,

day = "12",

doi = "10.1016/S0040-4039(00)00937-0",

language = "English",

volume = "41",

pages = "6429--6433",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "33",

}

TY - JOUR

T1 - Novel stereoselective construction of a quaternary carbon

T2 - Application to synthesis of the cyclopentenedione moiety of madindolines

AU - Hosokawa, S.

AU - Sekiguchi, K.

AU - Enemoto, M.

AU - Kobayashi, S.

N1 - Funding Information: We thank Prof. T. Sunazuka (Kitasato University) for helpful discussions. This work was supported in part by the Fujisawa Foundation (S.H.), Grant-in-Aid for Scientific Research from the Ministry of Education, Science, Sports, and Culture, Japan, and Shin-Etsu Chemical Co., Ltd.

PY - 2000/8/12

Y1 - 2000/8/12

N2 - Enantioselective synthesis of the cyclopentenedione moiety of madindolines was achieved. Stereoselective construction of a quaternary carbon was realized by alkylation of an enolate possessing chiral auxiliary. Cyclopentenedione was derived from a triketone precursor by intramolecular condensation. (C) 2000 Elsevier Science Ltd.

AB - Enantioselective synthesis of the cyclopentenedione moiety of madindolines was achieved. Stereoselective construction of a quaternary carbon was realized by alkylation of an enolate possessing chiral auxiliary. Cyclopentenedione was derived from a triketone precursor by intramolecular condensation. (C) 2000 Elsevier Science Ltd.

KW - Alkylation

KW - Cyclopentenedione

KW - Madindoline

KW - Quaternary carbon

UR - http://www.scopus.com/inward/record.url?scp=0034641497&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0034641497&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(00)00937-0

DO - 10.1016/S0040-4039(00)00937-0

M3 - Article

AN - SCOPUS:0034641497

SN - 0040-4039

VL - 41

SP - 6429

EP - 6433

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 33

ER -

Novel stereoselective construction of a quaternary carbon: Application to synthesis of the cyclopentenedione moiety of madindolines

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this