European Journal of Organic Chemistry
Copyright © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
A Diels–Alder Approach to a Communesin Model: A/B-Cyclization Route (Eur. J. Org. Chem. 16/2015)
The cover picture shows our approach to the communesin F model. A stereoselective Diels–Alder reaction is used for the formation of the vicinal quaternary stereocentres, while a chemoselective lactonization is employed for the differentiation of two primary amines. Our novel approach to the communesin ring system is based on initial formation of the A/B-rings followed by the D/E-rings, which allowed us to achieve the final hexacyclic structure. However, the desired bis-aminal could not be obtained due to an unexpected stability of the amidine functionality. We would like to thank Elisabet Bentmar for editing the cover and Michael Guiry for having provided the algae picture (© M. D. Guiry, seaweed.ie). 3441 ff.