Formal total synthesis of enigmazole A

Andreas Meissner; Takayuki Kishi; Yuka Fujisawa; Yuto Murai; Hiroyoshi Takamura; Isao Kadota

doi:10.1016/j.tetlet.2018.11.017

Formal total synthesis of enigmazole A

Andreas Meissner, Takayuki Kishi, Yuka Fujisawa, Yuto Murai, Hiroyoshi Takamura, Isao Kadota

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

4 Citations (Scopus)

Abstract

A stereoselective formal total synthesis of enigmazole A, a marine macrolide isolated from Cinachyrella enigmatica, is described. Lewis acid mediated intramolecular allylation of an α-acetoxy ether, prepared from alcohol and carboxylic acid fragments was carried out to construct the methylene THP ring with high stereoselectivity. The late-stage macrolactonization of the corresponding seco-acid provided a known synthetic intermediate of enigmazole A.

Original language	English
Pages (from-to)	4492-4495
Number of pages	4
Journal	Tetrahedron Letters
Volume	59
Issue number	51
DOIs	https://doi.org/10.1016/j.tetlet.2018.11.017
Publication status	Published - Dec 19 2018

Keywords

Allylation
Convergent synthesis
Enigmazole A
Macrolide
Reductive acetylation
Total synthesis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

UN SDGs

This output contributes to the following Sustainable Development Goal(s)

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10.1016/j.tetlet.2018.11.017

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title = "Formal total synthesis of enigmazole A",

abstract = "A stereoselective formal total synthesis of enigmazole A, a marine macrolide isolated from Cinachyrella enigmatica, is described. Lewis acid mediated intramolecular allylation of an α-acetoxy ether, prepared from alcohol and carboxylic acid fragments was carried out to construct the methylene THP ring with high stereoselectivity. The late-stage macrolactonization of the corresponding seco-acid provided a known synthetic intermediate of enigmazole A.",

keywords = "Allylation, Convergent synthesis, Enigmazole A, Macrolide, Reductive acetylation, Total synthesis",

author = "Andreas Meissner and Takayuki Kishi and Yuka Fujisawa and Yuto Murai and Hiroyoshi Takamura and Isao Kadota",

note = "Funding Information: We thank Professor A. B. Smith, III (University of Pennsylvania) for valuable discussion and suggestion. This work was financially supported by the Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology, Japan (No. 17K05863 ). Funding Information: We thank Professor A. B. Smith, III (University of Pennsylvania) for valuable discussion and suggestion. This work was financially supported by the Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology, Japan (No.17K05863). Publisher Copyright: {\textcopyright} 2018 Elsevier Ltd",

year = "2018",

month = dec,

day = "19",

doi = "10.1016/j.tetlet.2018.11.017",

language = "English",

volume = "59",

pages = "4492--4495",

journal = "Tetrahedron Letters",

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T1 - Formal total synthesis of enigmazole A

AU - Meissner, Andreas

AU - Kishi, Takayuki

AU - Fujisawa, Yuka

AU - Murai, Yuto

AU - Takamura, Hiroyoshi

AU - Kadota, Isao

N1 - Funding Information: We thank Professor A. B. Smith, III (University of Pennsylvania) for valuable discussion and suggestion. This work was financially supported by the Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology, Japan (No. 17K05863 ). Funding Information: We thank Professor A. B. Smith, III (University of Pennsylvania) for valuable discussion and suggestion. This work was financially supported by the Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology, Japan (No.17K05863). Publisher Copyright: © 2018 Elsevier Ltd

PY - 2018/12/19

Y1 - 2018/12/19

N2 - A stereoselective formal total synthesis of enigmazole A, a marine macrolide isolated from Cinachyrella enigmatica, is described. Lewis acid mediated intramolecular allylation of an α-acetoxy ether, prepared from alcohol and carboxylic acid fragments was carried out to construct the methylene THP ring with high stereoselectivity. The late-stage macrolactonization of the corresponding seco-acid provided a known synthetic intermediate of enigmazole A.

AB - A stereoselective formal total synthesis of enigmazole A, a marine macrolide isolated from Cinachyrella enigmatica, is described. Lewis acid mediated intramolecular allylation of an α-acetoxy ether, prepared from alcohol and carboxylic acid fragments was carried out to construct the methylene THP ring with high stereoselectivity. The late-stage macrolactonization of the corresponding seco-acid provided a known synthetic intermediate of enigmazole A.

KW - Allylation

KW - Convergent synthesis

KW - Enigmazole A

KW - Macrolide

KW - Reductive acetylation

KW - Total synthesis

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M3 - Article

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VL - 59

SP - 4492

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 51

ER -

Formal total synthesis of enigmazole A

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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