New Cuparene-Derived Sesquiterpenes with Unprecedented Oxygenation Patterns from the Sea Hare Aplysia dactylomela

Article abstract of DOI:10.1021/jo00367a021

Five new sesquiterpenes, cyclolaurene (2), cyclolaurenol (3), cyclolaurenol acetate (4), cupalaurenol (5), and cupalaurenol acetate (6), were isolated from the sea hare Aplysia dactylomela.Their structures including absolute configurations were deduced from spectroscopic data and chemical interconversion.The terpenes 3-6 are the first examples in which bromine and hydroxyl or acetoxy substituents are reversed in their positions from those usually found in related compounds, e.g., laurinterol (1).