Enantioselective total synthesis of idesolide via NaHCO3- promoted dimerization

Tomohiro Nagasawa; Naoyuki Shimada; Munefumi Torihata; Shigefumi Kuwahara

doi:10.1016/j.tet.2010.05.034

Enantioselective total synthesis of idesolide via NaHCO₃- promoted dimerization

Tomohiro Nagasawa, Naoyuki Shimada, Munefumi Torihata, Shigefumi Kuwahara

AGR - Bioscience and Biotechnology for Future Bioindustries

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

18 Citations (Scopus)

Abstract

The enantioselective total synthesis of idesolide has been accomplished in 20% overall yield from a known allylic alcohol by a nine-step sequence involving the Sharpless asymmetric epoxidation as the source of chirality and an efficient NaHCO₃-promoted dimerization of the monomeric form of idesolide as the key transformation.

Original language	English
Pages (from-to)	4965-4969
Number of pages	5
Journal	Tetrahedron
Volume	66
Issue number	27-28
DOIs	https://doi.org/10.1016/j.tet.2010.05.034
Publication status	Published - 2010 Jul 3

Keywords

Antiinflammatory
Dimerization
Idesolide
Spiro compounds
Total synthesis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tet.2010.05.034

Cite this

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title = "Enantioselective total synthesis of idesolide via NaHCO3- promoted dimerization",

abstract = "The enantioselective total synthesis of idesolide has been accomplished in 20% overall yield from a known allylic alcohol by a nine-step sequence involving the Sharpless asymmetric epoxidation as the source of chirality and an efficient NaHCO3-promoted dimerization of the monomeric form of idesolide as the key transformation.",

keywords = "Antiinflammatory, Dimerization, Idesolide, Spiro compounds, Total synthesis",

author = "Tomohiro Nagasawa and Naoyuki Shimada and Munefumi Torihata and Shigefumi Kuwahara",

note = "Funding Information: This work was financially supported, in part, by a Grant-in-Aid for Scientific Research (B) from the Ministry of Education, Culture, Sports, Science and Technology, Japan (No. 16380075 ). ",

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T1 - Enantioselective total synthesis of idesolide via NaHCO3- promoted dimerization

AU - Nagasawa, Tomohiro

AU - Shimada, Naoyuki

AU - Torihata, Munefumi

AU - Kuwahara, Shigefumi

N1 - Funding Information: This work was financially supported, in part, by a Grant-in-Aid for Scientific Research (B) from the Ministry of Education, Culture, Sports, Science and Technology, Japan (No. 16380075 ).

PY - 2010/7/3

Y1 - 2010/7/3

N2 - The enantioselective total synthesis of idesolide has been accomplished in 20% overall yield from a known allylic alcohol by a nine-step sequence involving the Sharpless asymmetric epoxidation as the source of chirality and an efficient NaHCO3-promoted dimerization of the monomeric form of idesolide as the key transformation.

AB - The enantioselective total synthesis of idesolide has been accomplished in 20% overall yield from a known allylic alcohol by a nine-step sequence involving the Sharpless asymmetric epoxidation as the source of chirality and an efficient NaHCO3-promoted dimerization of the monomeric form of idesolide as the key transformation.

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KW - Dimerization

KW - Idesolide

KW - Spiro compounds

KW - Total synthesis

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