Total Synthesis of the Lycorenine-Type Amaryllidaceae Alkaloid (±)-Clivonine via a Biomimetic Ring-Switch from a Lycorine-Type Progenitor

A fully diastereoselective total synthesis of the lycorenine-type Amaryllidaceae alkaloid (±)-clivonine (19) is reported via a route that employs for the first time a biomimetic ring-switch from a lycorine-type progenitor, thereby corroborating experimentally the biogenetic hypothesis first expounde...

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Published inJournal of the American Chemical Society Vol. 132; no. 14; pp. 5176 - 5178
Main Authors Giró Mañas, Carles, Paddock, Victoria L, Bochet, Christian G, Spivey, Alan C, White, Andrew J. P, Mann, Inderjit, Oppolzer, Wolfgang
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 14.04.2010
Amer Chemical Soc
Subjects
Amaryllidaceae Alkaloids - chemical synthesis
Amaryllidaceae Alkaloids - chemistry
Chemistry
Chemistry, Multidisciplinary
Crystallography, X-Ray
Cyclization
Models, Molecular
Molecular Structure
Phenanthridines - chemistry
Physical Sciences
Science & Technology
Stereoisomerism
TRANSFORMATION
(+/-)-TAZETTINE
INTERCONVERSIONS
(-)-HAEMANTHIDINE
(+/-)-HAEMANTHIDINE
(+)-PRETAZETTINE
STEREOCHEMISTRY
(+/-)-PRETAZETTINE
CLIVONINE
TAZETTINE
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Summary:A fully diastereoselective total synthesis of the lycorenine-type Amaryllidaceae alkaloid (±)-clivonine (19) is reported via a route that employs for the first time a biomimetic ring-switch from a lycorine-type progenitor, thereby corroborating experimentally the biogenetic hypothesis first expounded for these compounds by Barton in 1960.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:0002-7863
1520-5126
DOI:10.1021/ja910184j