Highly stereoselective synthesis of mupirocin H

Sandip Sengupta; Hak Joong Kim; Kyung Seon Cho; Woon Young Song; Taebo Sim

doi:10.1016/j.tet.2017.01.017

Highly stereoselective synthesis of mupirocin H

Sandip Sengupta, Hak Joong Kim, Kyung Seon Cho, Woon Young Song, Taebo Sim

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

5 Citations (Scopus)

Abstract

A highly diastereoselective and efficient convergent synthesis of mupirocin H starting from (+)-(R)-Roche ester was achieved. Grubbs cross metathesis was employed as the key step in the pathway to generate an important E-olefin intermediate. Other processes utilized in the route include a Pd-catalysed stereoselective substitution reaction of a cis epoxide, Sharpless epoxidation followed by Red-Al promoted epoxide ring opening, and Seebach methylation and a TEMPO/BAIB mediated oxidation-lactonization sequence. Finally, we observed that mupirocin H inhibits SbnE, a synthetase required for staphyloferrin B biosynthesis.

Original language	English
Pages (from-to)	1182-1189
Number of pages	8
Journal	Tetrahedron
Volume	73
Issue number	8
DOIs	https://doi.org/10.1016/j.tet.2017.01.017
Publication status	Published - 2017

Bibliographical note

Funding Information:
This work was supported by Korea Institute of Science and Technology, and the KU-KIST Graduate School of Converging Science and Technology Program, and KRF (Korea Research Fellowship) program and a grant (NRF-2015R1D1A1A01056815) of the National Research Foundation of Korea.

Publisher Copyright:
© 2017 Elsevier Ltd

Keywords

(+)-(R)-Roche ester
Grubbs cross metathesis
Mupirocin H
Total synthesis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2017.01.017

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title = "Highly stereoselective synthesis of mupirocin H",

abstract = "A highly diastereoselective and efficient convergent synthesis of mupirocin H starting from (+)-(R)-Roche ester was achieved. Grubbs cross metathesis was employed as the key step in the pathway to generate an important E-olefin intermediate. Other processes utilized in the route include a Pd-catalysed stereoselective substitution reaction of a cis epoxide, Sharpless epoxidation followed by Red-Al promoted epoxide ring opening, and Seebach methylation and a TEMPO/BAIB mediated oxidation-lactonization sequence. Finally, we observed that mupirocin H inhibits SbnE, a synthetase required for staphyloferrin B biosynthesis.",

keywords = "(+)-(R)-Roche ester, Grubbs cross metathesis, Mupirocin H, Total synthesis",

author = "Sandip Sengupta and Kim, {Hak Joong} and Cho, {Kyung Seon} and Song, {Woon Young} and Taebo Sim",

note = "Funding Information: This work was supported by Korea Institute of Science and Technology, and the KU-KIST Graduate School of Converging Science and Technology Program, and KRF (Korea Research Fellowship) program and a grant (NRF-2015R1D1A1A01056815) of the National Research Foundation of Korea. Publisher Copyright: {\textcopyright} 2017 Elsevier Ltd",

year = "2017",

doi = "10.1016/j.tet.2017.01.017",

language = "English",

volume = "73",

pages = "1182--1189",

journal = "Tetrahedron",

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publisher = "Elsevier Ltd",

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TY - JOUR

T1 - Highly stereoselective synthesis of mupirocin H

AU - Sengupta, Sandip

AU - Kim, Hak Joong

AU - Cho, Kyung Seon

AU - Song, Woon Young

AU - Sim, Taebo

N1 - Funding Information: This work was supported by Korea Institute of Science and Technology, and the KU-KIST Graduate School of Converging Science and Technology Program, and KRF (Korea Research Fellowship) program and a grant (NRF-2015R1D1A1A01056815) of the National Research Foundation of Korea. Publisher Copyright: © 2017 Elsevier Ltd

PY - 2017

Y1 - 2017

N2 - A highly diastereoselective and efficient convergent synthesis of mupirocin H starting from (+)-(R)-Roche ester was achieved. Grubbs cross metathesis was employed as the key step in the pathway to generate an important E-olefin intermediate. Other processes utilized in the route include a Pd-catalysed stereoselective substitution reaction of a cis epoxide, Sharpless epoxidation followed by Red-Al promoted epoxide ring opening, and Seebach methylation and a TEMPO/BAIB mediated oxidation-lactonization sequence. Finally, we observed that mupirocin H inhibits SbnE, a synthetase required for staphyloferrin B biosynthesis.

AB - A highly diastereoselective and efficient convergent synthesis of mupirocin H starting from (+)-(R)-Roche ester was achieved. Grubbs cross metathesis was employed as the key step in the pathway to generate an important E-olefin intermediate. Other processes utilized in the route include a Pd-catalysed stereoselective substitution reaction of a cis epoxide, Sharpless epoxidation followed by Red-Al promoted epoxide ring opening, and Seebach methylation and a TEMPO/BAIB mediated oxidation-lactonization sequence. Finally, we observed that mupirocin H inhibits SbnE, a synthetase required for staphyloferrin B biosynthesis.

KW - (+)-(R)-Roche ester

KW - Grubbs cross metathesis

KW - Mupirocin H

KW - Total synthesis

UR - http://www.scopus.com/inward/record.url?scp=85009739536&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2017.01.017

DO - 10.1016/j.tet.2017.01.017

M3 - Article

AN - SCOPUS:85009739536

SN - 0040-4020

VL - 73

SP - 1182

EP - 1189

JO - Tetrahedron

JF - Tetrahedron

IS - 8

ER -

Highly stereoselective synthesis of mupirocin H

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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