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Investigating biogenetic hypotheses of the securinega alkaloids: enantioselective total syntheses of secu’amamine E/ent-virosine A and bubbialine


Wehlauch, Robin; Grendelmeier, Simone M; Miyatake-Ondozabal, Hideki; Sandtorv, Alexander H; Scherer, Manuel; Gademann, Karl (2017). Investigating biogenetic hypotheses of the securinega alkaloids: enantioselective total syntheses of secu’amamine E/ent-virosine A and bubbialine. Organic Letters, 19(3):548-551.

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.

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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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:17 January 2017
Deposited On:22 Aug 2017 16:38
Last Modified:23 Aug 2017 07:33
Publisher:American Chemical Society (ACS)
ISSN:1523-7052
Additional Information:This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://pubs.acs.org/doi/abs/10.1021/acs.orglett.6b03716
Publisher DOI:https://doi.org/10.1021/acs.orglett.6b03716
PubMed ID:28094969

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