Total synthesis of the Amaryllidaceae alkaloid clivonine | Zendy

Helmut Haning | Zendy; C. Giro-Manas | Zendy; Victoria L. Paddock | Zendy; Christian G. Bochet | Zendy; Andrew J. P. White | Zendy; Gérald Bernardinelli | Zendy; Inderjit Mann | Zendy; Wolfang Oppolzer | Zendy; Alan C. Spivey | Zendy

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Total synthesis of the Amaryllidaceae alkaloid clivonine

Author(s) -

Helmut Haning,

C. Giro-Manas,

Victoria L. Paddock,

Christian G. Bochet,

Andrew J. P. White,

Gérald Bernardinelli,

Inderjit Mann,

Wolfang Oppolzer,

Alan C. Spivey

Publication year - 2011

Publication title -

organic and biomolecular chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.923

H-Index - 146

eISSN - 1477-0539

pISSN - 1477-0520

DOI - 10.1039/c0ob00895h

Subject(s) - amaryllidaceae , chemistry , amaryllidaceae alkaloids , alkaloid , ring (chemistry) , total synthesis , stereochemistry , organic chemistry , botany , biology

Two syntheses of the Amaryllidaceae alkaloid clivonine (1) are described. Both employ previously reported 7-arylhydrindane 6 as an intermediate but differ in the method employed for subsequent introduction of what becomes the ring-B lactone carbonyl carbon (C7). The synthesis featuring a Bischler-Napieralski reaction for this transformation constitutes the first asymmetric synthesis of natural (+)-clivonine. Crystal structures for compounds (±)-13, (±)-16, (-)-20 and (±)-28 are also reported.

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