Sporochnol, fish deterrent

Ohira, S., Kuboki, A., Hasegawa, T., Kikuchi, T., Kutsukake, T., and Nomura, M. (2002) Total synthesis of sporochnols, fish deterrents from a marine alga. Tetrahedron Lett, 43, 4641-4644. 

Kamikubo, T, Shimizu, M., and Ogasawara, K. (1997) Enantioconvergent tactic for the synthesis of (+)-sporochnol A, the fish deterrent from the Caribbean marine alga Sporochnus bolleanus. Enantiomer, 2, 297-301. 

Fadel, A. and Vandromme, L. (1999) Total synthesis of (—)-sporochnol A, the fish deterrent, from a chiral malonate. Tetrahedron Asymmetry, 10,1153-1162. 

Avila-Zarraga, J.G., Barroso, M., Covarrubias-Zuniga, A., and Romero-Ortega, M. (2005) A short synthesis of ( )-sporochnol A, a chemical fish deterrent from a Caribbean marine alga. Synth. Commun., 35, 389-395. 

A cyclobutene ROCM sequence was also used in a synthesis of racemic sporochnol (410), a naturally occurring feeding deterrent toward herbivorous fish (Scheme 80) [170]. Exposing cyclobutene 406 (0.01 M in boiling 1,2-dichloroethane) in the presence of ethylene to second-generation catalyst C (8 mol%) led to 1,5-diene 407 in 73% yield, along with 9% of the homodimer derived from 407 by involving the less hindered double bond. Site-selective hy-... 

---