Dysidazirine, a cytotoxic azacyclopropene from the marine sponge Dysidea fragilis

The Journal of Organic Chemistry
1988.0

Abstract

The cosmopolitan sponge Dysidea fragilis has been shown to produce several different sesquiterpenes and the nature of these natural products shows a marked geographic variation. For instance the sponge collected from Hawaii yielded the bicyclic sesquiterpenes upial and the nakafurans 8 and 9. Extraction of D. fragilis from Brittany, on the other hand, gave a series of sesquiterpenes based on the monocyclic sesquiterpene penlanfuran. In surprising contrast to these reports we have found that D. fragilis (Montagu, 1818) collected in Fiji contains no sesquiterpenes but a new cytotoxic azacyclopropene carboxylic acid ester, dysidazirine (1). This represents the first example of this ring strained class of heterocycles from a marine source and, to our knowledge, only the second reported naturally occurring 2H-azirine.

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