title: Stereocontrolled Access to Enantiopure 7-Substituted cis- and trans-Octahydroindoles.
abstract: Cyclocondensation of (R)-phenylglycinol with stereoisomeric mixtures (racemates, cis/trans) of 3-substituted 2-oxocyclohexaneacetates stereoselectively afforded tricyclic oxazoloindolone lactams, from which straightforward procedures for the stereocontrolled formation of enantiopure 7-substituted octahydroindoles with a variety of stereochemical patterns have been developed. The methodology has been successfully applied to the synthesis of (+)-α-lycorane.
authors: Laboratory of Organic Chemistry, Faculty of Pharmacy, and Institute of Biomedicine (IBUB), University of Barcelona , 080028-Barcelona, Spain.
authors: Elena
authors: E
authors: Ghirardi
authors: Laboratory of Organic Chemistry, Faculty of Pharmacy, and Institute of Biomedicine (IBUB), University of Barcelona , 080028-Barcelona, Spain.
authors: Rosa
authors: R
authors: Griera
authors: Laboratory of Organic Chemistry, Faculty of Pharmacy, and Institute of Biomedicine (IBUB), University of Barcelona , 080028-Barcelona, Spain.
authors: Miriam
authors: M
authors: Piccichè
authors: Institut de Ciència de Materials de Barcelona (ICMAB, CSIC), Campus UAB, 08193-Bellaterra, Spain.
authors: Elies
authors: E
authors: Molins
authors: Departamento de Química Orgánica I, Facultad de Ciencias Químicas, Centro de Innovación en Química Avanzada (ORFEO-CINQA), Universidad Complutense de Madrid , 28040-Madrid, Spain.
authors: Israel
authors: I
authors: Fernández
authors: Laboratory of Organic Chemistry, Faculty of Pharmacy, and Institute of Biomedicine (IBUB), University of Barcelona , 080028-Barcelona, Spain.
authors: Joan
authors: J
authors: Bosch
authors: Laboratory of Organic Chemistry, Faculty of Pharmacy, and Institute of Biomedicine (IBUB), University of Barcelona , 080028-Barcelona, Spain.
authors: Mercedes
authors: M
authors: Amat