Arenarol and Arenarone: Sesquiterpenoids with Rearranged Drimane Skeletons from the Marine Sponge Dysidea arenaria

Article abstract of DOI:10.1021/jo00176a005

Two new sesquiterpenoids, arenarol (3a) and arenarone (4), having identical rearranged drimane skeletons bearing hydroquinol and hydroquinone moieties,respectively, are reported from the Pacific sponge Dysidea arenaria.The structure of arenarol was determined by X-ray analysis of its diacetate which crystallizes in the space group P2₁2₁2₁ with unit-cell dimensions (138 K) a: 9.964 (5), b: 6.81 (2), and c: 33.33 (5) <*>. the crystal structure was determined from 2268 data.The final R value is 0.065.Arenarol was chemically correlated with arenarone by silver oxide oxidation.Detailed 400-MHz 1H NMR analysis of arenarol assisted by 2-D J-resolved and 2-D homocorrelation spectroscopy is tabulated.