title: Stereoselective synthesis of 12,13-cyclopropyl-epothilone B and side-chain-modified variants.
abstract: A general strategy has been devised for the stereoselective synthesis of 12,13-cyclopropyl-epothilone B and side-chain-modified variants thereof, which relies on late stage introduction of the heterocycle through Wittig olefination of ketone 14. Formation of the macrocycle was achieved through RCM-based ring closure and introduction of the cyclopropane moiety involved a highly selective Charette cyclopropanation of allylic alcohol 7.
authors.affiliation: Swiss Federal Institute of Technology (ETH) Zürich, HCI H405, Wolfgang-Pauli-Str. 10, CH-8093 Zürich, Switzerland.
authors.forename: Raphael
authors.initials: R
authors.lastname: Schiess
authors.forename: Jürg
authors.initials: J
authors.lastname: Gertsch
authors.forename: W Bernd
authors.initials: WB
authors.lastname: Schweizer
authors.forename: Karl-Heinz
authors.initials: KH
authors.lastname: Altmann
mesh_terms: D003521:Cyclopropanes / Q000737:chemistry*; D034261:Epothilones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D003521:Cyclopropanes; D034261:Epothilones; C030797:cyclopropane; C093788:epothilone B