Absolute Configuration of Symbiodinolactone A

The absolute configurations at five stereogenic centers
in symbiodinolactone
A, a 12-membered macrolide isolated from the symbiotic marine dinoflagellate Symbiodinium sp. associated with an acoelomorpha Amphiscolops sp., were determined to be 7R,11R,12R,13R,14R. A combination of different techniques was
applied in this regard such as Rychnovsky’s method, Kishi’s
universal NMR databases, the modified Mosher’s method, and
comparison of the NMR data of the bis(S)-MTPA ester
of a degradation product of symbiodinolactone A with those of synthesized
reference compounds. In addition, symbiodinolactone A was found to
exhibit cytotoxicity against L1210 murine leukemia cells.