volume 47 issue 11 pages 1547-1556

Total Syntheses of (–)-Alstolucines A, B, and F, (–)-Echitamidine, and (–)-N-Demethylalstogucine

Christiana Teijaro 1
Senzhi Zhao 1
Praveen Kokkonda 1
Rodrigo Andrade 1
Publication typeJournal Article
Publication date2015-04-09
scimago Q2
wos Q2
SJR0.559
CiteScore4.6
Impact factor2.3
ISSN00397881, 1437210X
Catalysis
Organic Chemistry
Abstract

The first enantioselective total syntheses of (–)-alstolucinces A, B, and F, (–)-echitamidine, and (–)-N-demethylalstogucine are reported. This article details the development of our first- and second-generation approaches toward the ABCE tetracyclic core of the strychnos alkaloids and the application thereof to the aforementioned targets. Key steps involve our sequential one-pot biscyclization method that constructs the C and E rings of the tetracyclic core and Rawal’s application of the intramolecular Heck reaction to secure the pentacyclic framework common amongst all targets.

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GOST Copy
Teijaro C. et al. Total Syntheses of (–)-Alstolucines A, B, and F, (–)-Echitamidine, and (–)-N-Demethylalstogucine // Synthesis. 2015. Vol. 47. No. 11. pp. 1547-1556.
GOST all authors (up to 50) Copy
Teijaro C., Zhao S., Kokkonda P., Andrade R. Total Syntheses of (–)-Alstolucines A, B, and F, (–)-Echitamidine, and (–)-N-Demethylalstogucine // Synthesis. 2015. Vol. 47. No. 11. pp. 1547-1556.
RIS |
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RIS Copy
TY - JOUR
DO - 10.1055/s-0034-1378698
UR - https://doi.org/10.1055/s-0034-1378698
TI - Total Syntheses of (–)-Alstolucines A, B, and F, (–)-Echitamidine, and (–)-N-Demethylalstogucine
T2 - Synthesis
AU - Teijaro, Christiana
AU - Zhao, Senzhi
AU - Kokkonda, Praveen
AU - Andrade, Rodrigo
PY - 2015
DA - 2015/04/09
PB - Georg Thieme Verlag KG
SP - 1547-1556
IS - 11
VL - 47
SN - 0039-7881
SN - 1437-210X
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2015_Teijaro,
author = {Christiana Teijaro and Senzhi Zhao and Praveen Kokkonda and Rodrigo Andrade},
title = {Total Syntheses of (–)-Alstolucines A, B, and F, (–)-Echitamidine, and (–)-N-Demethylalstogucine},
journal = {Synthesis},
year = {2015},
volume = {47},
publisher = {Georg Thieme Verlag KG},
month = {apr},
url = {https://doi.org/10.1055/s-0034-1378698},
number = {11},
pages = {1547--1556},
doi = {10.1055/s-0034-1378698}
}
MLA
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MLA Copy
Teijaro, Christiana, et al. “Total Syntheses of (–)-Alstolucines A, B, and F, (–)-Echitamidine, and (–)-N-Demethylalstogucine.” Synthesis, vol. 47, no. 11, Apr. 2015, pp. 1547-1556. https://doi.org/10.1055/s-0034-1378698.