Beilstein J. Org. Chem.2013,9, 1931–1935, doi:10.3762/bjoc.9.228
, Hiratsuka 259-1293, Japan 10.3762/bjoc.9.228 Abstract Symbiodinolide is a polyol marine natural product with a molecular weight of 2860. Herein, a streamlined synthesis of the C79–C97 fragment of symbiodinolide is described. In the synthetic route, a spiroacetalization, a Julia–Kocienski olefination, and a
Sharpless asymmetric dihydroxylation were utilized as the key transformations.
Keywords: Julia–Kocienski olefination; polyol marine natural product; Sharpless asymmetric dihydroxylation; spiroacetalization; symbiodinolide; Findings
A 62-membered polyol marine natural product, symbiodinolide (1, Figure 1
), was isolated from the 80% aqueous ethanol extract of the cultured symbiotic dinoflagellate Symbiodinium sp. in 2007 [1]. Symbiodinolide shows voltage-dependent N-type Ca2+ channel-opening activity at 7 nmol/L and COX-1 inhibitory effect at 2 μmol/L (65% inhibition). Furthermore, 1 ruptures the tissue