Isolation, structural elucidation, and synthesis of curcutetraol

The new natural products (+)-curcutetraol and (-)-curcutriolamide were isolated from the bacterium CNH-741 and the fungus CNC-979, isolated from marine sediment. (+)Curcutetraol is a polar compound and contains a tertiary benzylic alcohol moiety at the single stereogenic center, which was retained without racemization by avoiding chromatography on silica. The absolute configuration of (+)curcutetraol was determined by comparison of its experimental CD spectrum with the spectra predicted by quantum-chemical CD calculations. Phenolic bisabolane sesquiterpenoids from marine sources were previously known only from gorgonians and sponges. A short total synthesis of racemic curcutetraol has been developed. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005).