Total Synthesis of (-)-Strempeliopine.

Zeng, Xianhuang; Boger, Dale L

Zeng, Xianhuang; Boger, Dale L.

Afiliação

Zeng X; Department of Chemistry and the Skaggs Institute for Chemical Biology, the Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
Boger DL; Department of Chemistry and the Skaggs Institute for Chemical Biology, the Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States.

J Am Chem Soc ; 143(31): 12412-12417, 2021 08 11.

Article em En | MEDLINE | ID: mdl-34324817

ABSTRACT

ABSTRACT

A total synthesis of (-)-strempeliopine is disclosed that enlists a powerful SmI2-mediated and BF3·OEt2-initiated dearomative transannular radical cyclization onto an indole by an N-acyl α-aminoalkyl radical that is derived by single electron reduction of an in situ generated iminium ion for formation of a quaternary center and the strategic C19-C2 bond in its core structure.

Assuntos

Alcaloides Indólicos/síntese química; Ciclização; Alcaloides Indólicos/química; Conformação Molecular; Estereoisomerismo

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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Alcaloides Indólicos Idioma: En Revista: J Am Chem Soc Ano de publicação: 2021 Tipo de documento: Article País de afiliação: Estados Unidos

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