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An Efficient Synthesis of (+)-Anatoxin-a. by Marco Skrinjar; Carita Nilsson; Lars-G. Wistrand is a Chemistry article available to read on EtoBox.

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## An e#icient synthesis (38 % overall yield in 8 steps starting from 2) of the potent neurotoxin (+)-anatoxin-a is described. The key step involves the stereoselective addition of 5-hexenylcopper to the chiral N-acyliminium ion 2a. Anatoxin-a (l), isolated from the blue-green freshwater alga Anabaena Flos aquae, is one of the most powerful agonists of the nicotinic acetylcholine receptor known today. Of particular interest is the large difference in receptor binding affinities observed for the two enantiomers, the naturally occurring (+)enannomer being about 100 times more powerful. H N 0 W 1 The relative rigidity of the homotropane system makes 1 a suitable starting point for structure-activity studies of the nicotinic acetylcholine receptor. Synthetic approaches towards 1 are numerous\*, however, syntheses of enantiomerlcally pure (+)-1 have mainly been carried out by the Rapoport grou~.~" In our synthesis of (+)-1, we have utilized the highly selective trans addition of alkylcopper reagents to Me0 2 2a

Who reads An Efficient Synthesis of (+)-Anatoxin-a.?

Author

Marco Skrinjar; Carita Nilsson; Lars-G. Wistrand

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0957-4166)

Published

1992

Language

EN

Field

Chemistry (Physical Sciences)