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Published October 17, 2016 | Accepted Version + Supplemental Material
Journal Article Open

Enantioselective Pd-Catalyzed Allylic Alkylation Reactions of Dihydropyrido[1,2-a]indolone Substrates: Efficient Syntheses of (−)-Goniomitine, (+)-Aspidospermidine, and (−)-Quebrachamine


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.

Additional Information

© 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. Received: August 19, 2016; Revised: September 7, 2016; First published: 26 September 2016. The authors wish to thank NIH-NIGMS (R01GM080269), Amgen, the Gordon and Betty Moore Foundation, and Caltech for financial support. B.P.P. thanks the NSF for a predoctoral fellowship (Grant DGE-1144469). Y.N. thanks Toray Industries Inc. for a postdoctoral fellowship. The authors thank Mona Shahgholi and Naseem Torian for mass spectrometry assistance, and Dr. Scott Virgil (Caltech) and the Caltech Center for Catalysis and Chemical Synthesis, for instrumentation assistance.

Attached Files

Accepted Version - nihms835898.pdf

Supplemental Material - anie201608138-sup-0001-misc_information.pdf


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