Open Access
Total Syntheses of the C19 Diterpenoid Alkaloids (−)-Talatisamine, (−)-Liljestrandisine, and (−)-Liljestrandinine by a Fragment Coupling Approach
Alice R. Wong
1
,
Nicholas J Fastuca
1
,
Victor W. Mak
1
,
Jeffrey K Kerkovius
1
,
Susan M Stevenson
1
,
Sarah E Reisman
1
Publication type: Journal Article
Publication date: 2021-07-27
scimago Q1
wos Q1
SJR: 3.286
CiteScore: 19.3
Impact factor: 10.4
ISSN: 23747943, 23747951
PubMed ID:
34471676
General Chemistry
General Chemical Engineering
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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Total citations:
30
Citations from 2024:
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(43.33%)
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GOST
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Wong A. R. et al. Total Syntheses of the C19 Diterpenoid Alkaloids (−)-Talatisamine, (−)-Liljestrandisine, and (−)-Liljestrandinine by a Fragment Coupling Approach // ACS Central Science. 2021. Vol. 7. No. 8. pp. 1311-1316.
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Wong A. R., Fastuca N. J., Mak V. W., Kerkovius J. K., Stevenson S. M., Reisman S. E. Total Syntheses of the C19 Diterpenoid Alkaloids (−)-Talatisamine, (−)-Liljestrandisine, and (−)-Liljestrandinine by a Fragment Coupling Approach // ACS Central Science. 2021. Vol. 7. No. 8. pp. 1311-1316.
Cite this
RIS
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TY - JOUR
DO - 10.1021/acscentsci.1c00540
UR - https://doi.org/10.1021/acscentsci.1c00540
TI - Total Syntheses of the C19 Diterpenoid Alkaloids (−)-Talatisamine, (−)-Liljestrandisine, and (−)-Liljestrandinine by a Fragment Coupling Approach
T2 - ACS Central Science
AU - Wong, Alice R.
AU - Fastuca, Nicholas J
AU - Mak, Victor W.
AU - Kerkovius, Jeffrey K
AU - Stevenson, Susan M
AU - Reisman, Sarah E
PY - 2021
DA - 2021/07/27
PB - American Chemical Society (ACS)
SP - 1311-1316
IS - 8
VL - 7
PMID - 34471676
SN - 2374-7943
SN - 2374-7951
ER -
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BibTex (up to 50 authors)
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@article{2021_Wong,
author = {Alice R. Wong and Nicholas J Fastuca and Victor W. Mak and Jeffrey K Kerkovius and Susan M Stevenson and Sarah E Reisman},
title = {Total Syntheses of the C19 Diterpenoid Alkaloids (−)-Talatisamine, (−)-Liljestrandisine, and (−)-Liljestrandinine by a Fragment Coupling Approach},
journal = {ACS Central Science},
year = {2021},
volume = {7},
publisher = {American Chemical Society (ACS)},
month = {jul},
url = {https://doi.org/10.1021/acscentsci.1c00540},
number = {8},
pages = {1311--1316},
doi = {10.1021/acscentsci.1c00540}
}
Cite this
MLA
Copy
Wong, Alice R., et al. “Total Syntheses of the C19 Diterpenoid Alkaloids (−)-Talatisamine, (−)-Liljestrandisine, and (−)-Liljestrandinine by a Fragment Coupling Approach.” ACS Central Science, vol. 7, no. 8, Jul. 2021, pp. 1311-1316. https://doi.org/10.1021/acscentsci.1c00540.