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Conformational Bias in Macrocyclic Ethers and Observation of High Solvolytic Reactivity at a Masked Furfuryl (=2-Furylmethyl) C-Atom
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2000
Year
Bioorganic ChemistryEngineeringTurkish Mediterranean SeaMarine ChemistryOrganic ChemistryComputational ChemistryChemistryHeterocycle ChemistryBiophysicsMasked FurfurylBiochemistryReactivity (Chemistry)Macrocyclic EthersConformational BiasCommon OxygenationHeterocyclicNatural SciencesHalogenationSynthetic Chemistry
New polyhalogenated, twelve-membered, O-bridged cyclic C15-ethers, having in common oxygenation at C(6) and a bromoallene side chain at C(4) (where C(1) is the bromoallene-chain terminus), were isolated from the red seaweed Laurencia obtusa from the Turkish Mediterranean Sea, i.e., the 9,12-O-bridged obtusallene VII (5), the 6,9 : 9,12-bis-O-bridged obtusallene V (3) and obtusallene VI (4), as well as the 6,9-O-bridged obtusallene VIII (8) and obtusallene IX (9). The behavior of portions of the macrocycle involved in fast motions and their equilibrium position depend on the particular compound, revealing a subtle conformational behavior of these macrocycles, while 8 and 9 show an unprecedented solvolytic reactivity at the masked furfuryl (=2-furylmethyl) C-atom.