Synthesis of (±)-Crispine A via a nitrosoalkene hetero-diels-alder addition to ethyl vinyl ether

Gallos, John, Yioti, Efthymia, Mati, Ioulia, Arvanitidis, Athanassios, Massen, Zoe and Alexandraki, Elli 2010. Synthesis of (±)-Crispine A via a nitrosoalkene hetero-diels-alder addition to ethyl vinyl ether. Synthesis 2011 (01) , pp. 142-146. 10.1055/s-0030-1258333

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Abstract

The synthesis of (±)-crispine A in 9 steps and 24% overall­ yield was achieved using a nitrosoalkene hetero-Diels-Alder­ addition to ethyl vinyl ether as the key step. The synthesis starts from commercial 3,4-dimethoxyphenylacetic acid and uses simple methods, easily accessible materials and inexpensive reagents. An isochroman derivative was unexpectedly formed in an attempted reduction of a dihydro-4H-1,2-oxazine intermediate.

Item Type:	Article
Date Type:	Published Online
Status:	Published
Schools:	Chemistry
Publisher:	Thieme Publishing / Georg Thieme Verlag
ISSN:	0039-7881
Last Modified:	14 Dec 2020 02:23
URI:	https://orca.cardiff.ac.uk/id/eprint/122303

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