Stereocontrolled synthesis of the macrolactone core of neopeltolide

Andreas Meissner; Nobuhiro Tanaka; Hiroyoshi Takamura; Isao Kadota

doi:10.1016/j.tetlet.2018.12.066

Stereocontrolled synthesis of the macrolactone core of neopeltolide

Andreas Meissner, Nobuhiro Tanaka, Hiroyoshi Takamura, Isao Kadota

School of Science

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

7 Citations (Scopus)

Abstract

A stereoselective synthesis of the macrolactone core of neopeltolide is described. The tetrahydropyran moiety was constructed via the intramolecular allylation of an α-acetoxy ether. A late-stage macrolactonization provided a known synthetic intermediate of neopeltolide.

Original language	English
Pages (from-to)	432-434
Number of pages	3
Journal	Tetrahedron Letters
Volume	60
Issue number	5
DOIs	https://doi.org/10.1016/j.tetlet.2018.12.066
Publication status	Published - Jan 31 2019

Keywords

Allylation
Convergent synthesis
Macrolide
Neopeltolide
Reductive acetylation

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2018.12.066

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abstract = "A stereoselective synthesis of the macrolactone core of neopeltolide is described. The tetrahydropyran moiety was constructed via the intramolecular allylation of an α-acetoxy ether. A late-stage macrolactonization provided a known synthetic intermediate of neopeltolide.",

keywords = "Allylation, Convergent synthesis, Macrolide, Neopeltolide, Reductive acetylation",

author = "Andreas Meissner and Nobuhiro Tanaka and Hiroyoshi Takamura and Isao Kadota",

note = "Funding Information: This work was financially supported by JSPS KAKENHI (Grant Number 17K05863 ). Publisher Copyright: {\textcopyright} 2018 Elsevier Ltd",

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AU - Meissner, Andreas

AU - Tanaka, Nobuhiro

AU - Takamura, Hiroyoshi

AU - Kadota, Isao

PY - 2019/1/31

Y1 - 2019/1/31

N2 - A stereoselective synthesis of the macrolactone core of neopeltolide is described. The tetrahydropyran moiety was constructed via the intramolecular allylation of an α-acetoxy ether. A late-stage macrolactonization provided a known synthetic intermediate of neopeltolide.

AB - A stereoselective synthesis of the macrolactone core of neopeltolide is described. The tetrahydropyran moiety was constructed via the intramolecular allylation of an α-acetoxy ether. A late-stage macrolactonization provided a known synthetic intermediate of neopeltolide.

KW - Allylation

KW - Convergent synthesis

KW - Macrolide

KW - Neopeltolide

KW - Reductive acetylation

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 5

ER -

Stereocontrolled synthesis of the macrolactone core of neopeltolide

Abstract

Keywords

ASJC Scopus subject areas

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