Short Total Synthesis of (+/-)--Lycorane by a Sequential Intramolecular Acylal Cyclisation (IAC) and Intramolecular Heck Addition Reaction

An intramolecular acylal cyclisation (IAC) approach to the synthesis of a range of bicyclic heterocycles is reported. As an example of the utility of the IAC reaction, the methodology was applied in a protecting-group-free five-step total synthesis of (+/-)--lycorane, incorporating a new intramolecu...

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Published inChemistry : a European journal Vol. 23; no. 20; pp. 4750 - 4755
Main Authors Monaco, Alessandra, Szulc, Blanka R., Rao, Zenobia X., Barniol-Xicota, Marta, Sehailia, Moussa, Borges, Bruno M. A., Hilton, Stephen T.
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 06.04.2017
Wiley Subscription Services, Inc
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
lycoranes
GAMMA-LYCORANE
AMARYLLIDACEAE ALKALOIDS
LYCORINE-TYPE ALKALOIDS
CASCADE REACTIONS
HUMAN LEUKEMIA-CELLS
ONE-POT SYNTHESIS
Heck reaction
Lewis acids
FORMAL TOTAL-SYNTHESIS
erythrina
AROMATIC ERYTHRINA ALKALOIDS
RADICAL CYCLIZATIONS
tandem cyclisation
TETRACYCLIC FRAMEWORK
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Summary:An intramolecular acylal cyclisation (IAC) approach to the synthesis of a range of bicyclic heterocycles is reported. As an example of the utility of the IAC reaction, the methodology was applied in a protecting-group-free five-step total synthesis of (+/-)--lycorane, incorporating a new intramolecular Heck addition reaction to generate the pentacyclic core structure of the natural product in good yield.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 14
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201700143