title: A concise, phosphate-mediated approach to the total synthesis of (-)-tetrahydrolipstatin.
abstract: An efficient synthesis of (-)-tetrahydrolipstatin (THL) is reported. This method takes advantage of a phosphate tether-mediated, one-pot, sequential RCM/CM/hydrogenation protocol to deliver THL in eight total steps from a readily prepared (S,S)-triene. The strategy incorporates selective cross-metathesis, regioselective hydrogenation, regio- and diastereoselective cuprate addition, and Mitsunobu inversion for installation of the C5 formamide ester subunit.
authors.affiliation: Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045-7582, USA.
authors.forename: Phanindra K M
authors.initials: PK
authors.lastname: Venukadasula
authors.forename: Rambabu
authors.initials: R
authors.lastname: Chegondi
authors.forename: Soma
authors.initials: S
authors.lastname: Maitra
authors.forename: Paul R
authors.initials: PR
authors.lastname: Hanson
mesh_terms: D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D000077403:Orlistat; D010710:Phosphates / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D007783:Lactones; D010710:Phosphates; D000077403:Orlistat