Total synthesis and absolute configuration of koshikalide

Kazuki Kunifuda; Arihiro Iwasaki; Masashi Nagamoto; Kiyotake Suenaga

doi:10.1016/j.tetlet.2016.06.002

Total synthesis and absolute configuration of koshikalide

Kazuki Kunifuda, Arihiro Iwasaki, Masashi Nagamoto, Kiyotake Suenaga

Department of Chemistry

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

6 Citations (Scopus)

Abstract

The first total synthesis of koshikalide, a 14-membered macrolide that contains three olefins, was achieved. The skipped diene in the cyclic system was efficiently constructed by very mild Stille coupling at low temperature. The absolute stereochemistry was established by comparison of the specific optical rotations of natural and synthesized koshikalide.

Original language	English
Pages (from-to)	3121-3123
Number of pages	3
Journal	Tetrahedron Letters
Volume	57
Issue number	29
DOIs	https://doi.org/10.1016/j.tetlet.2016.06.002
Publication status	Published - 2016

Keywords

Koshikalide
Macrolide
Marine cyanobacteria
Marine natural products
Total synthesis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2016.06.002

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title = "Total synthesis and absolute configuration of koshikalide",

abstract = "The first total synthesis of koshikalide, a 14-membered macrolide that contains three olefins, was achieved. The skipped diene in the cyclic system was efficiently constructed by very mild Stille coupling at low temperature. The absolute stereochemistry was established by comparison of the specific optical rotations of natural and synthesized koshikalide.",

keywords = "Koshikalide, Macrolide, Marine cyanobacteria, Marine natural products, Total synthesis",

author = "Kazuki Kunifuda and Arihiro Iwasaki and Masashi Nagamoto and Kiyotake Suenaga",

note = "Funding Information: This work was supported by a Grant-in-Aid for Scientific Research (B) (No. 24310160) from the Japan Society for the Promotion of Science and the MEXT -Supported Program for the Strategic Research Foundation at Private Universities, 2009–2013 from the Ministry of Education, Culture, Sports, Science, and Technology , Japan. We thank Sanyo Fine Co., Ltd for their gift of chiral trityl glycidyl ether. Publisher Copyright: {\textcopyright} 2016 Elsevier Ltd",

year = "2016",

doi = "10.1016/j.tetlet.2016.06.002",

language = "English",

volume = "57",

pages = "3121--3123",

journal = "Tetrahedron Letters",

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publisher = "Elsevier Limited",

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TY - JOUR

T1 - Total synthesis and absolute configuration of koshikalide

AU - Kunifuda, Kazuki

AU - Iwasaki, Arihiro

AU - Nagamoto, Masashi

AU - Suenaga, Kiyotake

N1 - Funding Information: This work was supported by a Grant-in-Aid for Scientific Research (B) (No. 24310160) from the Japan Society for the Promotion of Science and the MEXT -Supported Program for the Strategic Research Foundation at Private Universities, 2009–2013 from the Ministry of Education, Culture, Sports, Science, and Technology , Japan. We thank Sanyo Fine Co., Ltd for their gift of chiral trityl glycidyl ether. Publisher Copyright: © 2016 Elsevier Ltd

PY - 2016

Y1 - 2016

N2 - The first total synthesis of koshikalide, a 14-membered macrolide that contains three olefins, was achieved. The skipped diene in the cyclic system was efficiently constructed by very mild Stille coupling at low temperature. The absolute stereochemistry was established by comparison of the specific optical rotations of natural and synthesized koshikalide.

AB - The first total synthesis of koshikalide, a 14-membered macrolide that contains three olefins, was achieved. The skipped diene in the cyclic system was efficiently constructed by very mild Stille coupling at low temperature. The absolute stereochemistry was established by comparison of the specific optical rotations of natural and synthesized koshikalide.

KW - Koshikalide

KW - Macrolide

KW - Marine cyanobacteria

KW - Marine natural products

KW - Total synthesis

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DO - 10.1016/j.tetlet.2016.06.002

M3 - Article

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SN - 0040-4039

VL - 57

SP - 3121

EP - 3123

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 29

ER -

Total synthesis and absolute configuration of koshikalide

Abstract

Keywords

ASJC Scopus subject areas

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