Synthesis of the spiroacetal fragments of spirofungins A and B, antibiotics isolated from Streptomyces violaceusniger Tü 4113

Hiroyuki Sakauchi; Emi Higashi; Yuko Shimizu; Mikiko Kojima; Yuko Asamitsu; Shigefumi Kuwahara; Minoru Izumi; Hiromasa Kiyota

doi:10.1515/hc-2015-0193

Synthesis of the spiroacetal fragments of spirofungins A and B, antibiotics isolated from Streptomyces violaceusniger Tü 4113

Hiroyuki Sakauchi, Emi Higashi, Yuko Shimizu, Mikiko Kojima, Yuko Asamitsu, Shigefumi Kuwahara, Minoru Izumi, Hiromasa Kiyota

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

Abstract

The spiroacetal [C(9)-C(20)] fragments of spirofungins A and B, antibiotics isolated from Streptomyces violaceusniger Tü 4113, were prepared from a known bromo alcohol derived from (S)-citronellal, using thermodynamically controlled iodolactonization and spiroacetalization as the key steps.

Original language	English
Pages (from-to)	337-343
Number of pages	7
Journal	Heterocyclic Communications
Volume	21
Issue number	6
DOIs	https://doi.org/10.1515/hc-2015-0193
Publication status	Published - Dec 1 2015

Keywords

Streptomyces violaceusniger Tü 4113
acetylide
antibiotics
iodolactonization
selenolactonization
spiroacetalization
spirofungins A and B
synthesis

ASJC Scopus subject areas

Organic Chemistry

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title = "Synthesis of the spiroacetal fragments of spirofungins A and B, antibiotics isolated from Streptomyces violaceusniger T{\"u} 4113",

abstract = "The spiroacetal [C(9)-C(20)] fragments of spirofungins A and B, antibiotics isolated from Streptomyces violaceusniger T{\"u} 4113, were prepared from a known bromo alcohol derived from (S)-citronellal, using thermodynamically controlled iodolactonization and spiroacetalization as the key steps.",

keywords = "Streptomyces violaceusniger T{\"u} 4113, acetylide, antibiotics, iodolactonization, selenolactonization, spiroacetalization, spirofungins A and B, synthesis",

author = "Hiroyuki Sakauchi and Emi Higashi and Yuko Shimizu and Mikiko Kojima and Yuko Asamitsu and Shigefumi Kuwahara and Minoru Izumi and Hiromasa Kiyota",

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year = "2015",

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doi = "10.1515/hc-2015-0193",

language = "English",

volume = "21",

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T1 - Synthesis of the spiroacetal fragments of spirofungins A and B, antibiotics isolated from Streptomyces violaceusniger Tü 4113

AU - Sakauchi, Hiroyuki

AU - Higashi, Emi

AU - Shimizu, Yuko

AU - Kojima, Mikiko

AU - Asamitsu, Yuko

AU - Kuwahara, Shigefumi

AU - Izumi, Minoru

AU - Kiyota, Hiromasa

PY - 2015/12/1

Y1 - 2015/12/1

N2 - The spiroacetal [C(9)-C(20)] fragments of spirofungins A and B, antibiotics isolated from Streptomyces violaceusniger Tü 4113, were prepared from a known bromo alcohol derived from (S)-citronellal, using thermodynamically controlled iodolactonization and spiroacetalization as the key steps.

AB - The spiroacetal [C(9)-C(20)] fragments of spirofungins A and B, antibiotics isolated from Streptomyces violaceusniger Tü 4113, were prepared from a known bromo alcohol derived from (S)-citronellal, using thermodynamically controlled iodolactonization and spiroacetalization as the key steps.

KW - Streptomyces violaceusniger Tü 4113

KW - acetylide

KW - antibiotics

KW - iodolactonization

KW - selenolactonization

KW - spiroacetalization

KW - spirofungins A and B

KW - synthesis

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JO - Heterocyclic Communications

JF - Heterocyclic Communications

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ER -

Synthesis of the spiroacetal fragments of spirofungins A and B, antibiotics isolated from Streptomyces violaceusniger Tü 4113

Abstract

Keywords

ASJC Scopus subject areas

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