Beau P Pritchett1, Jun Kikuchi1, Yoshitaka Numajiri1, Brian M Stoltz2. 1. Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Blvd. MC 101-20, Pasadena, CA, 91125, USA. 2. Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Blvd. MC 101-20, Pasadena, CA, 91125, USA. stoltz@caltech.edu.
Abstract
The successful application of dihydropyrido[1,2-a]indolone (DHPI) substrates in Pd-catalyzed asymmetric allylic alkylation chemistry facilitates rapid access to multiple alkaloid frameworks in an enantioselective fashion. Strategic bromination at the indole C3 position greatly improved the allylic alkylation chemistry and enabled a highly efficient Negishi cross-coupling downstream. The first catalytic enantioselective total synthesis of (-)-goniomitine, along with divergent formal syntheses of (+)-aspidospermidine and (-)-quebrachamine, are reported herein.
The successful application of dihydropyrido[1,2-a]indolone (n class="Chemical">DHPI) substrates in Pd-catalyzed asymmetric allylic alkylation chemistry facilitates rapid access to multiple alkaloid frameworks in an enantioselective fashion. Strategic bromination at the indole C3 position greatly improved the allylic alkylation chemistry and enabled a highly efficient Negishi cross-coupling downstream. The first catalytic enantioselective total synthesis of (-)-goniomitine, along with divergent formal syntheses of (+)-aspidospermidine and (-)-quebrachamine, are reported herein.
Authors: Anil S Guram; Anthony O King; John G Allen; Xianghong Wang; Laurie B Schenkel; Johann Chan; Emilio E Bunel; Margaret M Faul; Robert D Larsen; Michael J Martinelli; Paul J Reider Journal: Org Lett Date: 2006-04-27 Impact factor: 6.005
Authors: Katerina M Korch; Christian Eidamshaus; Douglas C Behenna; Sangkil Nam; David Horne; Brian M Stoltz Journal: Angew Chem Int Ed Engl Date: 2014-11-07 Impact factor: 15.336
Authors: Nathan B Bennett; Douglas C Duquette; Jimin Kim; Wen-Bo Liu; Alexander N Marziale; Douglas C Behenna; Scott C Virgil; Brian M Stoltz Journal: Chemistry Date: 2013-02-27 Impact factor: 5.236
Authors: Nicolas Fleury-Brégeot; Marc Presset; Floriane Beaumard; Virginie Colombel; Daniel Oehlrich; Frederik Rombouts; Gary A Molander Journal: J Org Chem Date: 2012-11-06 Impact factor: 4.354
Authors: Christopher E Reimann; Aurapat Ngamnithiporn; Kohei Hayashida; Daisuke Saito; Katerina M Korch; Brian M Stoltz Journal: Angew Chem Int Ed Engl Date: 2021-07-06 Impact factor: 16.823