Pritchett, Beau P. and Donckele, Etienne J. and Stoltz, Brian M. (2017) Enantioselective Catalysis Coupled with Stereodivergent Cyclization Strategies Enables Rapid Syntheses of (+)-Limaspermidine and (+)-Kopsihainanine A. Angewandte Chemie International Edition, 56 (41). pp. 12624-12627. ISSN 1433-7851. PMCID PMC5896324. doi:10.1002/anie.201707304. https://resolver.caltech.edu/CaltechAUTHORS:20170905-134054944
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Abstract
Enantioselective Pd-catalyzed allylic alkylations of dihydropyrido[1,2-a]indolone (DHPI) substrates were used to construct the C20-quaternary stereocenters of multiple monoterpene indole alkaloids. Stereodivergent Pictet–Spengler and Bischler–Napieralski cyclization/reduction cascades furnish the cis- and trans-fused azadecalin subunits present in Aspidosperma and Kopsia alkaloids, respectively, en route to highly efficient syntheses of (+)-limaspermidine and (+)-kopsihainanine A.
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Additional Information: | © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. Issue online: 27 September 2017; Version of record online: 5 September 2017; Manuscript Received: 18 July 2017. The authors wish to thank NIH-NIGMS (R01GM080269), Amgen, the Gordon and Betty Moore Foundation, the Caltech Center for Catalysis and Chemical Synthesis, and Caltech for financial support. B.P.P. thanks the NSF for a predoctoral fellowship (Grant DGE-1144469). E.J.D. thanks the Swiss National Science Foundation (SNSF) for a postdoctoral fellowship (Grant P2EZP2_168798). The authors thank Dr. Mona Shahgholi and Naseem Torian (Caltech) for mass spectrometry assistance, Dr. Scott Virgil (Caltech) for instrumentation assistance, and Larry Henling (Caltech) for X-ray crystallographic assistance. The authors declare no conflict of interest. | ||||||||||||||
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Subject Keywords: | allylic alkylation; asymmetric catalysis; monoterpene indole alkaloids; stereodivergent cyclizations; total synthesis | ||||||||||||||
Issue or Number: | 41 | ||||||||||||||
PubMed Central ID: | PMC5896324 | ||||||||||||||
DOI: | 10.1002/anie.201707304 | ||||||||||||||
Record Number: | CaltechAUTHORS:20170905-134054944 | ||||||||||||||
Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20170905-134054944 | ||||||||||||||
Official Citation: | B. P. Pritchett, E. J. Donckele, B. M. Stoltz, Angew. Chem. Int. Ed. 2017, 56, 12624. | ||||||||||||||
Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | ||||||||||||||
ID Code: | 81144 | ||||||||||||||
Collection: | CaltechAUTHORS | ||||||||||||||
Deposited By: | Tony Diaz | ||||||||||||||
Deposited On: | 05 Sep 2017 20:46 | ||||||||||||||
Last Modified: | 22 Mar 2022 19:34 |
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