Journal of Organic Chemistry p. 1475 - 1478 (1981)
Update date:2022-08-16
Topics:
Walker, Roger P.
Faulkner, John D.
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.
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