Divergent synthesis of pseudoenantiomers for ABC-ring moiety of steroids

Miyu Furuta; Kengo Hanaya; Takeshi Sugai; Mitsuru Shoji

doi:10.1016/j.tetlet.2014.04.018

Divergent synthesis of pseudoenantiomers for ABC-ring moiety of steroids

Miyu Furuta, Kengo Hanaya, Takeshi Sugai, Mitsuru Shoji

薬科学科

研究成果: Article › 査読

1 被引用数 (Scopus)

抄録

Steroid family has various bioactivities and characteristic polycyclic structure. Although several synthetic methods have been reported, more efficient way is desired for medicinal chemistry. In this Letter, we synthesized pseudoenantiomers of tricyclic enones toward both enantiomers for ABC-ring moiety of steroids utilizing d-mannitol as a chiral source. The key steps are radical domino cyclization of polyalkenyl-β-keto ester into tricyclic keto ester and subsequent dealkoxycarbonylation.

本文言語	English
ページ（範囲）	3189-3191
ページ数	3
ジャーナル	Tetrahedron Letters
巻	55
号	20
DOI	https://doi.org/10.1016/j.tetlet.2014.04.018
出版ステータス	Published - 2014 5 14

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

文献へのアクセス

10.1016/j.tetlet.2014.04.018

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引用スタイル

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title = "Divergent synthesis of pseudoenantiomers for ABC-ring moiety of steroids",

abstract = "Steroid family has various bioactivities and characteristic polycyclic structure. Although several synthetic methods have been reported, more efficient way is desired for medicinal chemistry. In this Letter, we synthesized pseudoenantiomers of tricyclic enones toward both enantiomers for ABC-ring moiety of steroids utilizing d-mannitol as a chiral source. The key steps are radical domino cyclization of polyalkenyl-β-keto ester into tricyclic keto ester and subsequent dealkoxycarbonylation.",

keywords = "Dealkoxycarbonylation, Domino reaction, Radical cyclization, Steroid, β-Keto ester",

author = "Miyu Furuta and Kengo Hanaya and Takeshi Sugai and Mitsuru Shoji",

note = "Funding Information: This work was supported by Platform for Drug Discovery, Informatics, and Structural Life Science from the Ministry of Education, Culture, Sports, Science, and Technology , Japan. We also thank Keio University Doctorate Student Grant-in-Aid Program 2012 (M.F.). ",

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T1 - Divergent synthesis of pseudoenantiomers for ABC-ring moiety of steroids

AU - Furuta, Miyu

AU - Hanaya, Kengo

AU - Sugai, Takeshi

AU - Shoji, Mitsuru

N1 - Funding Information: This work was supported by Platform for Drug Discovery, Informatics, and Structural Life Science from the Ministry of Education, Culture, Sports, Science, and Technology , Japan. We also thank Keio University Doctorate Student Grant-in-Aid Program 2012 (M.F.).

PY - 2014/5/14

Y1 - 2014/5/14

N2 - Steroid family has various bioactivities and characteristic polycyclic structure. Although several synthetic methods have been reported, more efficient way is desired for medicinal chemistry. In this Letter, we synthesized pseudoenantiomers of tricyclic enones toward both enantiomers for ABC-ring moiety of steroids utilizing d-mannitol as a chiral source. The key steps are radical domino cyclization of polyalkenyl-β-keto ester into tricyclic keto ester and subsequent dealkoxycarbonylation.

AB - Steroid family has various bioactivities and characteristic polycyclic structure. Although several synthetic methods have been reported, more efficient way is desired for medicinal chemistry. In this Letter, we synthesized pseudoenantiomers of tricyclic enones toward both enantiomers for ABC-ring moiety of steroids utilizing d-mannitol as a chiral source. The key steps are radical domino cyclization of polyalkenyl-β-keto ester into tricyclic keto ester and subsequent dealkoxycarbonylation.

KW - Dealkoxycarbonylation

KW - Domino reaction

KW - Radical cyclization

KW - Steroid

KW - β-Keto ester

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