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 | Zendy

D'Ambrosio Michele | Zendy; Mealli Carlo | Zendy; Guerriero Antonio | Zendy; Pietra Francesco | Zendy

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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

Author(s) -

D'Ambrosio Michele,

Mealli Carlo,

Guerriero Antonio,

Pietra Francesco

Publication year - 1985

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19850680536

Subject(s) - chemistry , sponge , biogenesis , stereochemistry , natural product , phenol , acetylation , biochemistry , organic chemistry , gene , botany , biology

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.

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