title: A Modular Formal Total Synthesis of (±)-Cycloclavine.
abstract: 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.
authors.affiliation: Institute of Organic Chemistry, University of Mainz , Duesbergweg 10-14, D-55128 Mainz, Germany.
authors.forename: Natalie
authors.initials: N
authors.lastname: Netz
authors.affiliation: Institute of Organic Chemistry, University of Mainz , Duesbergweg 10-14, D-55128 Mainz, Germany.
authors.forename: Till
authors.initials: T
authors.lastname: Opatz
mesh_terms: D000478:Alkylation; D019086:Bridged Bicyclo Compounds, Heterocyclic; D003500:Cyclization; D006586:Hexanes / Q000737:chemistry*; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: C532932:3-azabicyclo(3.1.0)hexane; D019086:Bridged Bicyclo Compounds, Heterocyclic; D006586:Hexanes; D026121:Indole Alkaloids; C560517:cycloclavine; C026385:n-hexane