TOBACCO CHEMISTRY .82. 7 NEW CEMBRANE-DERIVED COMPOUNDS FROM TOBACCO

Seven new cembrane-derived compounds (1-7) have been isolated from tobacco. They have been identified as (4E)-3-hydroxy-6-isopropyl-3-methyl-9-(5-oxotetrahydrofuran-2-yl)-4,9-decadienoic acid (1), (2R,4S,5E,7S)-2-hydroxy-7-isopropyl-4-methyl-10-oxo-5-undecen-4-olide (2), the (2R*,4R*,5E)- and (2R*,4S*,5E)-1,4-epoxy-2-hydroxy-7-isopropyl-4-methyl-5-undecen-10-ones 3 and 4, the (2S*,5R*)- and (2R*,5R*)-2,5-epidioxy-2-hydroxy-5-isopropyl-3-nonen-8-ones 5 and 6 and (2R*,4S*,5E)-2-hydroxy-7-isopropyl-4-methyl-5-nonen-4-olide (7) by spectral methods and, in the case of 2, also by biomimetic synthesis. The biogenesis of the new compounds is discussed.