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Enantioselective Catalysis Coupled with Stereodivergent Cyclization Strategies Enables Rapid Syntheses of (+)-Limaspermidine and (+)-Kopsihainanine A

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. 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.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1002/anie.201707304DOIArticle
http://onlinelibrary.wiley.com/doi/10.1002/anie.201707304/abstractPublisherArticle
ORCID:
AuthorORCID
Stoltz, Brian M.0000-0001-9837-1528
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.
Funders:
Funding AgencyGrant Number
NIHR01GM080269
AmgenUNSPECIFIED
Gordon and Betty Moore FoundationUNSPECIFIED
CaltechUNSPECIFIED
NSF Graduate Research FellowshipDGE-1144469
Swiss National Science Foundation (SNSF)P2EZP2_168798
Subject Keywords:allylic alkylation; asymmetric catalysis; monoterpene indole alkaloids; stereodivergent cyclizations; total synthesis
Issue or Number:41
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:03 Oct 2019 18:39

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