title: Transannular O-heterocyclization: a useful tool for the total synthesis of Murisolin and 16,19-cis-Murisolin.
abstract: Transannular O-heterocyclization is applied as a key step in a total synthesis. This highly stereoselective and metal-free transformation introduces four stereocenters in one step. It was chosen to be the pivotal step in the synthesis of Murisolin and 16,19-cis-Murisolin, two annonaceous acetogenins. The efficiency of this synthesis is further illustrated by a stereodivergent late-stage separation of both synthetic routes.
authors.affiliation: Westfälische Wilhelms-Universität Münster, Organisch-Chemisches Institut, Corrensstrasse 40, D-48149 Münster, Germany.
authors.forename: Peter
authors.initials: P
authors.lastname: Persich
authors.forename: Julia
authors.initials: J
authors.lastname: Kerschbaumer
authors.forename: Sandra
authors.initials: S
authors.lastname: Helling
authors.forename: Barbara
authors.initials: B
authors.lastname: Hildmann
authors.forename: Birgit
authors.initials: B
authors.lastname: Wibbeling
authors.forename: Günter
authors.initials: G
authors.lastname: Haufe
mesh_terms: D054378:Acetogenins / Q000737:chemistry*; D002175:Candida / Q000201:enzymology; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D008049:Lipase / Q000378:metabolism; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D054378:Acetogenins; D005663:Furans; D007783:Lactones; C507543:murisolin; D008049:Lipase