Convergent total synthesis of (−)-dactylolide

Tokihiro Tanaka; Yuto Murai; Takayuki Kishi; Hiroyoshi Takamura; Isao Kadota

doi:10.1016/j.tetlet.2018.01.034

Convergent total synthesis of (−)-dactylolide

Tokihiro Tanaka, Yuto Murai, Takayuki Kishi, Hiroyoshi Takamura, Isao Kadota

School of Science

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

10 Citations (Scopus)

Abstract

A convergent total synthesis of (−)-dactylolide is described. Constructing the 2,6-disubstituted exo-methylene THP moiety was achieved by the intramolecular allylation of α-acetoxy ether. The cyclization precursor was prepared from two segments, an alcohol and carboxylic acid derivatives, by esterification followed by reductive acetylation.

Original language	English
Pages (from-to)	763-766
Number of pages	4
Journal	Tetrahedron Letters
Volume	59
Issue number	8
DOIs	https://doi.org/10.1016/j.tetlet.2018.01.034
Publication status	Published - Feb 21 2018

Keywords

Allylation
Convergent synthesis
Dactylolide
Macrolide
Reductive acetylation
Total synthesis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2018.01.034

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title = "Convergent total synthesis of (−)-dactylolide",

abstract = "A convergent total synthesis of (−)-dactylolide is described. Constructing the 2,6-disubstituted exo-methylene THP moiety was achieved by the intramolecular allylation of α-acetoxy ether. The cyclization precursor was prepared from two segments, an alcohol and carboxylic acid derivatives, by esterification followed by reductive acetylation.",

keywords = "Allylation, Convergent synthesis, Dactylolide, Macrolide, Reductive acetylation, Total synthesis",

author = "Tokihiro Tanaka and Yuto Murai and Takayuki Kishi and Hiroyoshi Takamura and Isao Kadota",

note = "Funding Information: This work was financially supported by the Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology in Japan. Publisher Copyright: {\textcopyright} 2018 Elsevier Ltd",

year = "2018",

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doi = "10.1016/j.tetlet.2018.01.034",

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T1 - Convergent total synthesis of (−)-dactylolide

AU - Tanaka, Tokihiro

AU - Murai, Yuto

AU - Kishi, Takayuki

AU - Takamura, Hiroyoshi

AU - Kadota, Isao

N1 - Funding Information: This work was financially supported by the Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology in Japan. Publisher Copyright: © 2018 Elsevier Ltd

PY - 2018/2/21

Y1 - 2018/2/21

N2 - A convergent total synthesis of (−)-dactylolide is described. Constructing the 2,6-disubstituted exo-methylene THP moiety was achieved by the intramolecular allylation of α-acetoxy ether. The cyclization precursor was prepared from two segments, an alcohol and carboxylic acid derivatives, by esterification followed by reductive acetylation.

AB - A convergent total synthesis of (−)-dactylolide is described. Constructing the 2,6-disubstituted exo-methylene THP moiety was achieved by the intramolecular allylation of α-acetoxy ether. The cyclization precursor was prepared from two segments, an alcohol and carboxylic acid derivatives, by esterification followed by reductive acetylation.

KW - Allylation

KW - Convergent synthesis

KW - Dactylolide

KW - Macrolide

KW - Reductive acetylation

KW - Total synthesis

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DO - 10.1016/j.tetlet.2018.01.034

M3 - Article

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SN - 0040-4039

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EP - 766

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 8

ER -

Convergent total synthesis of (−)-dactylolide

Abstract

Keywords

ASJC Scopus subject areas

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