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

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

1 Citation (Scopus)

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.

Original language	English
Pages (from-to)	3189-3191
Number of pages	3
Journal	Tetrahedron Letters
Volume	55
Issue number	20
DOIs	https://doi.org/10.1016/j.tetlet.2014.04.018
Publication status	Published - 2014 May 14
Externally published	Yes

Keywords

Dealkoxycarbonylation
Domino reaction
Radical cyclization
Steroid
β-Keto ester

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tetlet.2014.04.018

Cite this

@article{91e7b23454d540b1af4d591a3741b42a,

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.). ",

year = "2014",

month = may,

day = "14",

doi = "10.1016/j.tetlet.2014.04.018",

language = "English",

volume = "55",

pages = "3189--3191",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "20",

}

TY - JOUR

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

UR - http://www.scopus.com/inward/record.url?scp=84899963866&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84899963866&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2014.04.018

DO - 10.1016/j.tetlet.2014.04.018

M3 - Article

AN - SCOPUS:84899963866

VL - 55

SP - 3189

EP - 3191

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 20

ER -

Divergent synthesis of pseudoenantiomers for ABC-ring moiety of steroids

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this