Asymmetric Total Synthesis of Biphenylquinolizidine Alkaloids 4â³-O-Demethyllythridine and 14-epi-4â³-O-Demethyllythridine.

Kawabata, Haruka; Hirama, Taku; Yanagisawa, Tomomi; Sato, Keigo; Kogure, Noriyuki; Kitajima, Mariko; Takayama, Hiromitsu

Asymmetric Total Synthesis of Biphenylquinolizidine Alkaloids 4â³-O-Demethyllythridine and 14-epi-4â³-O-Demethyllythridine.

Kawabata, Haruka; Hirama, Taku; Yanagisawa, Tomomi; Sato, Keigo; Kogure, Noriyuki; Kitajima, Mariko; Takayama, Hiromitsu.

Afiliação

Kawabata H; Graduate School of Pharmaceutical Sciences , Chiba University , 1-8-1 Inohana , Chuo-ku, Chiba 260-8675 , Japan.
Hirama T; Graduate School of Pharmaceutical Sciences , Chiba University , 1-8-1 Inohana , Chuo-ku, Chiba 260-8675 , Japan.
Yanagisawa T; Graduate School of Pharmaceutical Sciences , Chiba University , 1-8-1 Inohana , Chuo-ku, Chiba 260-8675 , Japan.
Sato K; Graduate School of Pharmaceutical Sciences , Chiba University , 1-8-1 Inohana , Chuo-ku, Chiba 260-8675 , Japan.
Kogure N; Graduate School of Pharmaceutical Sciences , Chiba University , 1-8-1 Inohana , Chuo-ku, Chiba 260-8675 , Japan.
Kitajima M; Graduate School of Pharmaceutical Sciences , Chiba University , 1-8-1 Inohana , Chuo-ku, Chiba 260-8675 , Japan.
Takayama H; Graduate School of Pharmaceutical Sciences , Chiba University , 1-8-1 Inohana , Chuo-ku, Chiba 260-8675 , Japan.

Org Lett ; 21(19): 7982-7986, 2019 10 04.

Article em En | MEDLINE | ID: mdl-31524399

ABSTRACT

ABSTRACT

The first asymmetric total synthesis of new biphenylquinolizidine alkaloids 4â³-O-demethyllythridine and 14-epi-4â³-O-demethyllythridine isolated from Heimia salicifolia was accomplished. The key steps in the synthesis were a copper(I)-catalyzed asymmetric intramolecular aza-Michael reaction to build a chiral 4-arylquinolizidine unit and an intramolecular Suzuki-Miyaura cross-coupling reaction to construct a macrolactone ring comprising a biphenyl moiety.

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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: Org Lett Assunto da revista: BIOQUIMICA Ano de publicação: 2019 Tipo de documento: Article País de afiliação: Japão

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