Tobacco Chemistry. 51. New Cembranic Diterpenoids from Greek Tobacco.

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Abstract
The isolation of (1S,2E,4R,6R,7E,11S,12S)-11,12-epoxy-2,7-cembradiene-4-,6-diol** (1), the (1S,2E,4R,6E,8R,11S,12E)- and (1S,2E,4S,6E,8R,11S,12E)-8,11-epoxy-2,6,12-cembratrien-4-ols (2, 3) and (1S,2E,4R,6E,8R,11S)-8,11-epoxy-2,6,12(20)-cembratrien-4-ol (4) from Greek tobacco is reported. Of these 1 is a new natural product, whereas 2-4, previously found in other tobacco varieties, are new to Greek tobacco. The structure of 1 was determined by synthesis and X-ray analysis of the corresponding mono-acetate 5. Compounds 2 and 3 have been correlated by dehydration and compound 4 was used as the starting material for a synthesis which confirms that the structure of a previously isolated tobacco dipterpenoid is (1S,2E,4R,6E,8R,11S,12R)-8,11-epoxy-2,6-cembradiene-4,12-diol (6). The acid rearrangement of 1, a reaction which is proposed to mimic the biogenesis of some of the 8,11- and 8,12-epoxy bridged tobacco cembranoids, is discussed.
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