title: The total synthesis of (-)-nitidasin.
abstract: Nitidasin is a pentacyclic sesterterpenoid with a rare 5-8-6-5 carbon skeleton that was isolated from the Peruvian folk medicine "Hercampuri". It belongs to a small class of sesterterpenoids that feature an isopropyl trans-hydrindane moiety fused to a variety of other ring systems. As a first installment of our general approach toward these natural products, we report the total synthesis of the title compound. Our stereoselective, convergent route involves the addition of a complex alkenyl lithium compound to a trans-hydrindanone, followed by chemoselective epoxidation, ring-closing olefin metathesis, and redox adjustment.
authors: Department of Chemistry and Center for Integrated Protein Science, Ludwig-Maximilians-Universität München, Butenandtstr. 5-13, 81377 München (Germany) http://www.cup.uni-muenchen.de/oc/trauner/
authors: Daniel T
authors: DT
authors: Hog
authors: Florian M E
authors: FM
authors: Huber
authors: Peter
authors: P
authors: Mayer
authors: Dirk
authors: D
authors: Trauner
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D054830:Sesterterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D001688:Biological Products; D054830:Sesterterpenes
keywords: ring-closing olefin metathesis; sesterterpenoids; stereoselective synthesis; total synthesis