6533b828fe1ef96bd12885d1
RESEARCH PRODUCT
A Modular Formal Total Synthesis of (±)-Cycloclavine
Till OpatzNatalie Netzsubject
CycloclavineAlkylationMolecular Structure010405 organic chemistryOrganic ChemistryTotal synthesisStereoisomerismStereoisomerismAlkylationBridged Bicyclo Compounds Heterocyclic010402 general chemistry01 natural sciencesCoupling reactionIndole Alkaloids0104 chemical sciencesHexanechemistry.chemical_compoundchemistryCyclizationHeck reactionYield (chemistry)HexanesOrganic chemistrydescription
Cycloclavine is a clavine-type Ergot alkaloid noteworthy for its unique pentacyclic skeleton featuring a 3-azabicyclo[3.1.0]hexane substructure. A short convergent route to the racemic alkaloid is described which comprises only eight linear steps and requires only four chromatographic purifications. The two key building blocks can be prepared in high yield from commercially available starting materials. Two consecutive coupling reactions, namely a selective alkylation of a dienolate and a Heck reaction, are the key steps of the reaction sequence.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2016-02-04 | The Journal of Organic Chemistry |