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ChemInform Abstract: Total Syntheses of (.+-.)-Agelasimine-A (VII), (.+-.)-Agelasimine-B ( VIII), and (.+-.)-Purino-diterpene (XI) and the Structure of Diacetylagelasimine-A (IX).

✍ Scribed by M. OHBA; N. KAWASE; T. FUJII

Publisher: John Wiley and Sons
Year: 2010
Weight: 35 KB
Volume: 28
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199702157

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✦ Synopsis

Total Syntheses of (±)-Agelasimine-A (VII), (±)-Agelasimine-B ( VIII), and (±)-Purino-diterpene (XI) and the Structure of Diacetylagelasimine-A (IX). -Central synthetic feature of the total syntheses of (VII) and (VIII), isolated from the marine sponge Agelas mauritiana includes the stereoselective preparation of the diol (VI), a key intermediate for their common diterpene portion. The reaction of (VII) with Ac2O in Py yields the imidazole (IX), which corresponds to diacetylagelasimine-A, initially assigned to the purine form (X). A similar acetylation of ( VIII) affords (XI).

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