✦ LIBER ✦
7-Bromocavernicolenone, a New α-Bromoenone from the Mediterranean Sponge Aplysina (= Verongia) cavernicola. Implied, Unprecedented Involvement of a Halogenated Dopa in the Biogenesis of a Natural Product
✍ Scribed by Michele D'Ambrosio; Carlo Mealli; Antonio Guerriero; Francesco Pietra
- Publisher
- John Wiley and Sons
- Year
- 1985
- Tongue
- German
- Weight
- 499 KB
- Volume
- 68
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
Abstract
A novel, mildly antibacterial, α‐bromoenone (7‐bromocavernicolenone) has been isolated from the Mediterranean sponge Aplysina (= Verongia) cavernicola. Its structure, 7‐bromo‐1,5‐dihydroxy‐2‐azabicyclo[3.3.1]non‐6‐en‐3,8‐dione (3), is based on X‐ray and NMR analysis and on the observation that acetylation of 3 affords two monoacetates. An unprecedented phenol oxidative biogenetic pathway is suggested leading to 7‐bromocavernicolenone via 3‐bromotyrosine and 5‐bromodopa.