cycloclavine and n-hexane

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.

Topics: Alkylation; Bridged Bicyclo Compounds, Heterocyclic; Cyclization; Hexanes; Indole Alkaloids; Molecular Structure; Stereoisomerism