Stereoselective synthesis of the C17–C29 fragment of amphidinolide N

Yuki Fujishima; Yusuke Ogura; Ryo Towada; Masaru Enomoto; Shigefumi Kuwahara

doi:10.1016/j.tetlet.2016.10.038

Stereoselective synthesis of the C17–C29 fragment of amphidinolide N

Yuki Fujishima, Yusuke Ogura, Ryo Towada, Masaru Enomoto, Shigefumi Kuwahara

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

8 Citations (Scopus)

Abstract

An enantio- and diastereoselective synthesis of the C17–C29 fragment of amphidinolide N, an extremely potent macrocyclic cytotoxin of marine origin, has been accomplished from a known olefinic ester by a 10-step sequence that involves a ring opening of a chiral epoxide with a dithiane derivative to construct the full carbon skeleton, a highly diastereoselective reduction of a β-hydroxy ketone intermediate to install the C21 asymmetric center, and a one-pot Sharpless AD/cyclization sequence to form a trans-substituted tetrahydrofuran ring system.

Original language	English
Pages (from-to)	5240-5242
Number of pages	3
Journal	Tetrahedron Letters
Volume	57
Issue number	47
DOIs	https://doi.org/10.1016/j.tetlet.2016.10.038
Publication status	Published - 2016

Keywords

Amphidinolide
Cytotoxic
Macrolide
Partial synthesis
Polyketide

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

UN SDGs

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

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10.1016/j.tetlet.2016.10.038

Cite this

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title = "Stereoselective synthesis of the C17–C29 fragment of amphidinolide N",

abstract = "An enantio- and diastereoselective synthesis of the C17–C29 fragment of amphidinolide N, an extremely potent macrocyclic cytotoxin of marine origin, has been accomplished from a known olefinic ester by a 10-step sequence that involves a ring opening of a chiral epoxide with a dithiane derivative to construct the full carbon skeleton, a highly diastereoselective reduction of a β-hydroxy ketone intermediate to install the C21 asymmetric center, and a one-pot Sharpless AD/cyclization sequence to form a trans-substituted tetrahydrofuran ring system.",

keywords = "Amphidinolide, Cytotoxic, Macrolide, Partial synthesis, Polyketide",

author = "Yuki Fujishima and Yusuke Ogura and Ryo Towada and Masaru Enomoto and Shigefumi Kuwahara",

note = "Funding Information: This work was financially supported by JSPS KAKENHI (No. 26292056 ). We thank Ms. Yuka Taguchi (Tohoku University) for her help in NMR and MS measurements. Publisher Copyright: {\textcopyright} 2016 Elsevier Ltd",

year = "2016",

doi = "10.1016/j.tetlet.2016.10.038",

language = "English",

volume = "57",

pages = "5240--5242",

journal = "Tetrahedron Letters",

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number = "47",

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TY - JOUR

T1 - Stereoselective synthesis of the C17–C29 fragment of amphidinolide N

AU - Fujishima, Yuki

AU - Ogura, Yusuke

AU - Towada, Ryo

AU - Enomoto, Masaru

AU - Kuwahara, Shigefumi

N1 - Funding Information: This work was financially supported by JSPS KAKENHI (No. 26292056 ). We thank Ms. Yuka Taguchi (Tohoku University) for her help in NMR and MS measurements. Publisher Copyright: © 2016 Elsevier Ltd

PY - 2016

Y1 - 2016

N2 - An enantio- and diastereoselective synthesis of the C17–C29 fragment of amphidinolide N, an extremely potent macrocyclic cytotoxin of marine origin, has been accomplished from a known olefinic ester by a 10-step sequence that involves a ring opening of a chiral epoxide with a dithiane derivative to construct the full carbon skeleton, a highly diastereoselective reduction of a β-hydroxy ketone intermediate to install the C21 asymmetric center, and a one-pot Sharpless AD/cyclization sequence to form a trans-substituted tetrahydrofuran ring system.

AB - An enantio- and diastereoselective synthesis of the C17–C29 fragment of amphidinolide N, an extremely potent macrocyclic cytotoxin of marine origin, has been accomplished from a known olefinic ester by a 10-step sequence that involves a ring opening of a chiral epoxide with a dithiane derivative to construct the full carbon skeleton, a highly diastereoselective reduction of a β-hydroxy ketone intermediate to install the C21 asymmetric center, and a one-pot Sharpless AD/cyclization sequence to form a trans-substituted tetrahydrofuran ring system.

KW - Amphidinolide

KW - Cytotoxic

KW - Macrolide

KW - Partial synthesis

KW - Polyketide

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DO - 10.1016/j.tetlet.2016.10.038

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VL - 57

SP - 5240

EP - 5242

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 47

ER -

Stereoselective synthesis of the C17–C29 fragment of amphidinolide N

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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