Total synthesis of 13-demethyllyngbyaloside B

Haruhiko Fuwa; Naoya Yamagata; Asami Saito; Makoto Sasaki

doi:10.1021/ol400408w

Total synthesis of 13-demethyllyngbyaloside B

Haruhiko Fuwa, Naoya Yamagata, Asami Saito, Makoto Sasaki

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

19 Citations (Scopus)

Abstract

Total synthesis of 13-demethyllyngbyaloside B, an unnatural analogue of a marine macrolide glycoside lyngbyaloside B, has been achieved. The 14-membered macrocyclic backbone was constructed in a convergent manner via esterification and ring-closing metathesis. The bromodiene side chain was introduced by means of a Stille-type reaction and a subsequent bromodesilylation. Finally, the rhamnopyranose unit was stereoselectively introduced by glycosylation under Schmidt conditions.

Original language	English
Pages (from-to)	1630-1633
Number of pages	4
Journal	Organic letters
Volume	15
Issue number	7
DOIs	https://doi.org/10.1021/ol400408w
Publication status	Published - 2013 Apr 5

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1021/ol400408w

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AU - Fuwa, Haruhiko

AU - Yamagata, Naoya

AU - Saito, Asami

AU - Sasaki, Makoto

PY - 2013/4/5

Y1 - 2013/4/5

N2 - Total synthesis of 13-demethyllyngbyaloside B, an unnatural analogue of a marine macrolide glycoside lyngbyaloside B, has been achieved. The 14-membered macrocyclic backbone was constructed in a convergent manner via esterification and ring-closing metathesis. The bromodiene side chain was introduced by means of a Stille-type reaction and a subsequent bromodesilylation. Finally, the rhamnopyranose unit was stereoselectively introduced by glycosylation under Schmidt conditions.

AB - Total synthesis of 13-demethyllyngbyaloside B, an unnatural analogue of a marine macrolide glycoside lyngbyaloside B, has been achieved. The 14-membered macrocyclic backbone was constructed in a convergent manner via esterification and ring-closing metathesis. The bromodiene side chain was introduced by means of a Stille-type reaction and a subsequent bromodesilylation. Finally, the rhamnopyranose unit was stereoselectively introduced by glycosylation under Schmidt conditions.

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Total synthesis of 13-demethyllyngbyaloside B

Abstract

ASJC Scopus subject areas

UN SDGs

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