Absolute configuration of halisulfate 3 from the sponge Ircinia sp

✍ Scribed by Elmar L. Müller; D.John Faulkner

• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 264 KB
• Volume: 53
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(97)00202-0

✦ Synopsis

The absolute configuration of halisulfate 3 (1), a metabolite of the sponge Ircinia sp. from the Philippines, was determined in two steps. The (13S) absolute configuration was derived by application of the chiral amide method using acid 5. The (8R.9S) stereochemistry of the bicyclic ring system was obtained by comparison of the optical rotation of the degradation product 8 with that of an ester 9 of known absolute configuration.