Total synthesis of janadolide

Daisuke Ojima; Hitomi Mine; Arihiro Iwasaki; Kiyotake Suenaga

doi:10.1016/j.tetlet.2018.02.034

Total synthesis of janadolide

Daisuke Ojima, Hitomi Mine, Arihiro Iwasaki, Kiyotake Suenaga

Department of Chemistry

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

5 Citations (Scopus)

Abstract

The first total synthesis of janadolide, a new cyclic polyketide-peptide hybrid possessing a tert-butyl group, is described. The synthesis of an unsaturated hydroxycarboxylic acid was effected via the lithiation of vinyl iodide followed by addition to a Weinreb amide with a tert-butyl group and stereoselective 1,2-reduction. The cyclic structure was constructed by macrolactamization at the amide bond between the proline moiety and fatty acid moiety.

Original language	English
Pages (from-to)	1360-1362
Number of pages	3
Journal	Tetrahedron Letters
Volume	59
Issue number	14
DOIs	https://doi.org/10.1016/j.tetlet.2018.02.034
Publication status	Published - 2018 Apr 4

Keywords

Depsipeptide
Macrolactamization
Total synthesis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2018.02.034

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title = "Total synthesis of janadolide",

abstract = "The first total synthesis of janadolide, a new cyclic polyketide-peptide hybrid possessing a tert-butyl group, is described. The synthesis of an unsaturated hydroxycarboxylic acid was effected via the lithiation of vinyl iodide followed by addition to a Weinreb amide with a tert-butyl group and stereoselective 1,2-reduction. The cyclic structure was constructed by macrolactamization at the amide bond between the proline moiety and fatty acid moiety.",

keywords = "Depsipeptide, Macrolactamization, Total synthesis",

author = "Daisuke Ojima and Hitomi Mine and Arihiro Iwasaki and Kiyotake Suenaga",

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T1 - Total synthesis of janadolide

AU - Ojima, Daisuke

AU - Mine, Hitomi

AU - Iwasaki, Arihiro

AU - Suenaga, Kiyotake

N1 - Funding Information: This work was supported by JSPS KAKENHI Grant Number 16H03285. Funding Information: This work was supported by JSPS KAKENHI Grant Number 16H03285 . A Publisher Copyright: © 2018 Elsevier Ltd

PY - 2018/4/4

Y1 - 2018/4/4

N2 - The first total synthesis of janadolide, a new cyclic polyketide-peptide hybrid possessing a tert-butyl group, is described. The synthesis of an unsaturated hydroxycarboxylic acid was effected via the lithiation of vinyl iodide followed by addition to a Weinreb amide with a tert-butyl group and stereoselective 1,2-reduction. The cyclic structure was constructed by macrolactamization at the amide bond between the proline moiety and fatty acid moiety.

AB - The first total synthesis of janadolide, a new cyclic polyketide-peptide hybrid possessing a tert-butyl group, is described. The synthesis of an unsaturated hydroxycarboxylic acid was effected via the lithiation of vinyl iodide followed by addition to a Weinreb amide with a tert-butyl group and stereoselective 1,2-reduction. The cyclic structure was constructed by macrolactamization at the amide bond between the proline moiety and fatty acid moiety.

KW - Depsipeptide

KW - Macrolactamization

KW - Total synthesis

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

Total synthesis of janadolide

Abstract

Keywords

ASJC Scopus subject areas

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