Chlorinated Acetylenes from the Nudibranch Diaulula sandiegensis

Article abstract of DOI:10.1021/jo00320a046

The nudibranch mollusc Diaulula sandiegensis contained nine chlorinated acetylenes, 1-9, all of which were relatively unstable when purified.The nine metabolites were identified as (1Z,3E,9Z)-1-chlorohexadeca-5,7-diyne-1,3,9-trien-15-one (1), (1Z,3Z,9Z)-1-chlorohexadeca-5,7-diyne-1,3,9-trien-15-one (2), (1Z,3E,9Z)-1-chlorohexadeca-5,7-diyne-1,3,9-trien-15-ol (3), (1Z,3Z,9Z)-1-chlorohexadeca-5,7-diyne-1,3,9-trien-15-ol (4), (1E,3E,9Z)-1-chlorohexadeca-5,7-diyne-1,3,9-trien-15-ol (5), (1Z,3E,9Z)-1-chlorohexadeca-5,7-diyne-1,3,9-trien-14-ol (6), (1Z,3Z,9Z)-1-chlorohexadeca-5,7-diyne-1,3,9-trien-14-ol (7), (1E,3E,9Z)-1-chlorohexadeca-5,7-diyne-1,3,9-trien-14-ol (8), and (1Z,3E)-1-chlorohexadeca-1,3-diene-5,7-diyn-14-ol (9) by analysis of spectral data.The chlorinated acetylenes 1-9 are believed to be involved in the chemical defense mechanism of the nudibranch.