Investigating Biogenetic Hypotheses of the Securinega Alkaloids: Enantioselective Total Syntheses of Secu’amamine E/ent-Virosine A and Bubbialine
Publication type: Journal Article
Publication date: 2017-01-17
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
28094969
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
The synthesis of the Securinega alkaloid secu'amamine E (ent-virosine A) has been accomplished for the first time in 12 steps and 8.5% overall yield. In addition, bubbialine has been prepared and characterized. These two alkaloids and bubbialidine, all featuring an azabicyclo[2.2.2]octane core, were rearranged to their azabicyclo[3.2.1]octane congeners, a framework found in many Securinega alkaloids. These experiments suggest that azabicyclo[2.2.2]octane derivatives could serve as intermediates in the biosynthesis of the rearranged azabicyclo[3.2.1]octane products.
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Citations from 2024:
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GOST
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Wehlauch R. et al. Investigating Biogenetic Hypotheses of the Securinega Alkaloids: Enantioselective Total Syntheses of Secu’amamine E/ent-Virosine A and Bubbialine // Organic Letters. 2017. Vol. 19. No. 3. pp. 548-551.
GOST all authors (up to 50)
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Wehlauch R., Grendelmeier S. M., Miyatake Ondozabal H., Sandtorv A. H., Scherer M., Gademann K. Investigating Biogenetic Hypotheses of the Securinega Alkaloids: Enantioselective Total Syntheses of Secu’amamine E/ent-Virosine A and Bubbialine // Organic Letters. 2017. Vol. 19. No. 3. pp. 548-551.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/acs.orglett.6b03716
UR - https://doi.org/10.1021/acs.orglett.6b03716
TI - Investigating Biogenetic Hypotheses of the Securinega Alkaloids: Enantioselective Total Syntheses of Secu’amamine E/ent-Virosine A and Bubbialine
T2 - Organic Letters
AU - Wehlauch, Robin
AU - Grendelmeier, Simone M
AU - Miyatake Ondozabal, Hideki
AU - Sandtorv, Alexander H
AU - Scherer, Manuel
AU - Gademann, Karl
PY - 2017
DA - 2017/01/17
PB - American Chemical Society (ACS)
SP - 548-551
IS - 3
VL - 19
PMID - 28094969
SN - 1523-7060
SN - 1523-7052
ER -
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BibTex (up to 50 authors)
Copy
@article{2017_Wehlauch,
author = {Robin Wehlauch and Simone M Grendelmeier and Hideki Miyatake Ondozabal and Alexander H Sandtorv and Manuel Scherer and Karl Gademann},
title = {Investigating Biogenetic Hypotheses of the Securinega Alkaloids: Enantioselective Total Syntheses of Secu’amamine E/ent-Virosine A and Bubbialine},
journal = {Organic Letters},
year = {2017},
volume = {19},
publisher = {American Chemical Society (ACS)},
month = {jan},
url = {https://doi.org/10.1021/acs.orglett.6b03716},
number = {3},
pages = {548--551},
doi = {10.1021/acs.orglett.6b03716}
}
Cite this
MLA
Copy
Wehlauch, Robin, et al. “Investigating Biogenetic Hypotheses of the Securinega Alkaloids: Enantioselective Total Syntheses of Secu’amamine E/ent-Virosine A and Bubbialine.” Organic Letters, vol. 19, no. 3, Jan. 2017, pp. 548-551. https://doi.org/10.1021/acs.orglett.6b03716.