The absolute configuration of (+)-sporochnol A, the fish deterrent from the Caribbean marine alga Sporochnus bolleanus

✍ Scribed by Michiyasu Takahashi; Yoko Shioura; Taku Murakami; Kunio Ogasawara

• Publisher: Elsevier Science
• Year: 1997
• Tongue: English
• Weight: 576 KB
• Volume: 8
• Category: Article
• ISSN: 0957-4166
• DOI: 10.1016/s0957-4166(97)00119-5

✦ Synopsis

The absolute configuration of (+)-sporochnol A, the fish deterrent from the Caribbean marine alga Sporochnus bolleanus, has been established as S based on the stereocontrolled synthesis of its (R)-(-)-enantiomer from (S)-epichlorohydrin. (~) 1997 Elsevier Science Ltd (+)-Sporochnol A 1 was isolated from the Caribbean marine alga Sporochnus bolleanus and it was shown to exhibit significant feeding deterrence toward herbivorous fishes. L Its structure was determined by spectral and chemical methods but left the absolute configuration uncertain. Since we are interested in its functions in chemical defense, we investigated its asymmetric synthesis using optically active epichlorohydrin 2 which are practically available in both enantiomeric forms. 2 We now disclose the enantiocontrolled synthesis of the unnatural (R)-(-)-enantiomer ent-1 which determined unambiguously the absolute configuration of natural (+)-sporochnol A 1 as S by correlation to the configuration of (S)-epichlorohydrin 2 (Scheme 1).

• chiral epichlorohydrin (2) (+)-sporochnol A (1)

Scheme 1.