Synthesis of (-)-sordarin

Shunsuke Chiba; Mitsuru Kitamura; Koichi Narasaka

doi:10.1021/ja060408h

Synthesis of (-)-sordarin

Shunsuke Chiba, Mitsuru Kitamura, Koichi Narasaka^*

^*Corresponding author for this work

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

96 Citations (Scopus)

Abstract

The first total synthesis of (-)-sordarin (1) was accomplished exploiting the following key reactions: (i) Ag(I)-catalyzed oxidative radical cyclization of a cyclopropanol derivative leading to a bicyclo-[5.3.0]decan-3-one skeleton; (ii) Pd(0)-catalyzed intramolecular allylation reaction resulting in the entire strained bicyclo[2.2.1]heptan-2-one framework of sordaricin (2); (iii) selective dihydroxylation of terminal alkenes by the combined use of OsO₄ and PhB(OH)₂; and (iv) β(1,2-cis)-selective glycosidation via a 1,3-anchimeric assistance from a 4-methoxybenzoyl group.

Original language	English
Pages (from-to)	6931-6937
Number of pages	7
Journal	Journal of the American Chemical Society
Volume	128
Issue number	21
DOIs	https://doi.org/10.1021/ja060408h
Publication status	Published - May 31 2006
Externally published	Yes

ASJC Scopus Subject Areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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abstract = "The first total synthesis of (-)-sordarin (1) was accomplished exploiting the following key reactions: (i) Ag(I)-catalyzed oxidative radical cyclization of a cyclopropanol derivative leading to a bicyclo-[5.3.0]decan-3-one skeleton; (ii) Pd(0)-catalyzed intramolecular allylation reaction resulting in the entire strained bicyclo[2.2.1]heptan-2-one framework of sordaricin (2); (iii) selective dihydroxylation of terminal alkenes by the combined use of OsO4 and PhB(OH)2; and (iv) β(1,2-cis)-selective glycosidation via a 1,3-anchimeric assistance from a 4-methoxybenzoyl group.",

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AU - Chiba, Shunsuke

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AU - Narasaka, Koichi

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AB - The first total synthesis of (-)-sordarin (1) was accomplished exploiting the following key reactions: (i) Ag(I)-catalyzed oxidative radical cyclization of a cyclopropanol derivative leading to a bicyclo-[5.3.0]decan-3-one skeleton; (ii) Pd(0)-catalyzed intramolecular allylation reaction resulting in the entire strained bicyclo[2.2.1]heptan-2-one framework of sordaricin (2); (iii) selective dihydroxylation of terminal alkenes by the combined use of OsO4 and PhB(OH)2; and (iv) β(1,2-cis)-selective glycosidation via a 1,3-anchimeric assistance from a 4-methoxybenzoyl group.

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Synthesis of (-)-sordarin

Abstract

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