First Total Syntheses of TetracenomycinsâC and X.

Sato, Shogo; Sakata, Keiichiro; Hashimoto, Yoshimitsu; Takikawa, Hiroshi; Suzuki, Keisuke

First Total Syntheses of TetracenomycinsâC and X.

Sato, Shogo; Sakata, Keiichiro; Hashimoto, Yoshimitsu; Takikawa, Hiroshi; Suzuki, Keisuke.

Afiliação

Sato S; Department of Chemistry, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo, 152-8551, Japan.
Sakata K; Department of Chemistry, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo, 152-8551, Japan.
Hashimoto Y; Department of Chemistry, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo, 152-8551, Japan.
Takikawa H; Present address: Showa Pharmaceutical University, 3-3165 Higashi-Tamagawagakuen, Machida, Tokyo, 194-8543, Japan.
Suzuki K; Department of Chemistry, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo, 152-8551, Japan.

Angew Chem Int Ed Engl ; 56(41): 12608-12613, 2017 10 02.

Article em En | MEDLINE | ID: mdl-28762249

ABSTRACT

ABSTRACT

The first total syntheses of tetracenomycinsâC and X were achieved, featuring 1)âpreparation of a hexasubstituted naphthonitrile oxide by successive benzyne cycloadditions and an oxidative ring-opening reaction; 2)âa novel ortho-quinone mono-acetal as the A-ring unit; 3)âconstruction of three contiguous stereogenic centers by an asymmetric benzoin cyclization, an isoxazole oxidation, and a stereoselective reduction.

Palavras-chave

antibiotics; asymmetric synthesis; benzyne; isoxazoles; nitrile oxide

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Texto completo: 1 Base de dados: MEDLINE Idioma: En Ano de publicação: 2017 Tipo de documento: Article

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