Recent progress in the synthesis of homotropane alkaloids adaline, euphococcinine and N-methyleuphococcinine

A - Papers appearing in refereed journals

Lima, D. J. P., Santana, A. E. G., Birkett, M. A. and Porto, R. S. 2021. Recent progress in the synthesis of homotropane alkaloids adaline, euphococcinine and N-methyleuphococcinine. Beilstein Journal of Organic Chemistry. 17, pp. 28-41. https://doi.org/10.3762/bjoc.17.4

AuthorsLima, D. J. P., Santana, A. E. G., Birkett, M. A. and Porto, R. S.
Abstract

The 9-azabicyclo[3.3.1]nonane ring system is present in several insect- and plant-derived alkaloids. (−)-Adaline (1) and (+)-euphococcinine (2), found in secretions of Coccinelid beetles, and (+)-N-methyleuphococcinine (3), isolated from the Colorado blue spruce Picea pungens, are members of this alkaloid family. Their unique bicyclic system with a quaternary stereocenter, and the potent biological activity exerted by these homotropane alkaloids, make them attractive synthetic targets. This work aims briefly to review the chemical ecology of Adalia bipunctata and the recent methodologies to obtain adaline (1), euphococcinine (2), and
N-methyleuphococcinine (3).

Keywords9-azabicyclo[3.3.1]nonane; Coccinelid beetles; Dipolar cycloaddition; Homotropane; Ring-closing metathesis
Year of Publication2021
JournalBeilstein Journal of Organic Chemistry
Journal citation17, pp. 28-41
Digital Object Identifier (DOI)https://doi.org/10.3762/bjoc.17.4
Open accessPublished as ‘gold’ (paid) open access
FunderBiotechnology and Biological Sciences Research Council
Funder project or codeBBSRC Strategic Programme in Smart Crop Protection
Publisher's version
Output statusPublished
Publication dates
Online05 Jan 2021
Publication process dates
Accepted27 Nov 2020

Permalink - https://repository.rothamsted.ac.uk/item/9834x/recent-progress-in-the-synthesis-of-homotropane-alkaloids-adaline-euphococcinine-and-n-methyleuphococcinine

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