Wong, Alice R. and Fastuca, Nicholas J. and Mak, Victor W. and Kerkovius, Jeffrey K. and Stevenson, Susan M. and Reisman, Sarah E. (2021) Total Syntheses of the C₁₉ Diterpenoid Alkaloids (–)-Talatisamine, (–)-Liljestrandisine, and (–)-Liljestrandinine by a Fragment Coupling Approach. ACS Central Science, 7 (8). pp. 1311-1316. ISSN 2374-7951. PMCID PMC8393236. doi:10.1021/acscentsci.1c00540. https://resolver.caltech.edu/CaltechAUTHORS:20210513-103036703
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Abstract
The C19 diterpenoid alkaloids (C19 DTAs) are a large family of natural products, many of which modulate the activity of ion channels in vivo and are therefore of interest for the study of neurological and cardiovascular diseases. The complex architectures of these molecules continue to challenge the state-of-the art in chemical synthesis, particularly with respect to efficient assembly of their polcyclic ring systems. Here, we report the total syntheses of (−)-talatisamine, (−)-liljestrandisine, and (−)-liljestrandinine, three aconitine-type C19 DTAs, using a fragment coupling strategy. Key to this approach is a 1,2-addition/semipinacol rearrangement sequence which efficiently joins two complex fragments and sets an all-carbon quaternary center.
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Alternate Title: | Total Syntheses of the C19 Diterpenoid Alkaloids (–)-Talatisamine, (–)-Liljestrandisine, and (–)-Liljestrandinine by a Fragment Coupling Approach | |||||||||||||||
Additional Information: | © 2021 The Authors. Published by American Chemical Society. Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0). Received: May 5, 2021; Published: July 27, 2021. Dr. Scott Virgil and the Caltech Center for Catalysis and Chemical Synthesis are gratefully acknowledged for access to analytical equipment. Fellowship support was provided by the NSF (V.W.M., A.R.W., Grant No. DGE-1144469), Natural Sciences and Engineering Research Council of Canada (J.K.K., Grant No. 532535), and the NIH (F32 GM122386 to S.M.S. and T32 GM07616 to N.J.F.). S.E.R. is a Heritage Medical Research Institute Investigator and acknowledges financial support from the NIH (R35GM118191). The authors declare no competing financial interest. | |||||||||||||||
Group: | Heritage Medical Research Institute | |||||||||||||||
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Subject Keywords: | Redox reactions, Alcohols, Anions, Rearrangement, Ketones | |||||||||||||||
Issue or Number: | 8 | |||||||||||||||
PubMed Central ID: | PMC8393236 | |||||||||||||||
DOI: | 10.1021/acscentsci.1c00540 | |||||||||||||||
Record Number: | CaltechAUTHORS:20210513-103036703 | |||||||||||||||
Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20210513-103036703 | |||||||||||||||
Official Citation: | Total Syntheses of the C19 Diterpenoid Alkaloids (−)-Talatisamine, (−)-Liljestrandisine, and (−)-Liljestrandinine by a Fragment Coupling Approach. Alice R. Wong, Nicholas J. Fastuca, Victor W. Mak, Jeffrey K. Kerkovius, Susan M. Stevenson, and Sarah E. Reisman. ACS Central Science 2021 7 (8), 1311-1316; DOI: 10.1021/acscentsci.1c00540 | |||||||||||||||
Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | |||||||||||||||
ID Code: | 109113 | |||||||||||||||
Collection: | CaltechAUTHORS | |||||||||||||||
Deposited By: | Tony Diaz | |||||||||||||||
Deposited On: | 13 May 2021 17:49 | |||||||||||||||
Last Modified: | 02 Sep 2021 16:03 |
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