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Stereoselective Synthesis of (+)-Annuionone A and (-)-Annuionone B
Lizhen Jiang1, Xiaojing Liu1, Po Yuan1
1Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University , Chengdu 610064, People's Republic of China.
Abstract:
A stereoselective synthetic approach was utilized to synthesize enantiopure annuionones A (1b) and B (2b), two ionone-type norsesquiterpenoids that both bear a 6-oxabicyclo[3.2.1]octane framework and possess allelopathic activity. A stereoselective Diels-Alder reaction based on chiral trisubstituted dienophile 20 was employed to obtain the optically active polysubstituted cyclohexane core of both natural products. Using this approach, (+)-annuionone A (1b) and (-)-annuionone B (2b) were synthesized from lactol (+)-15 in 10% overall yield.
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