Stereoselective Synthesis of (+)-Annuionone A and (-)-Annuionone B.
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.
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University , Chengdu 610064, People's Republic of China.
Lizhen
L
Jiang
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University , Chengdu 610064, People's Republic of China.
Xiaojing
X
Liu
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University , Chengdu 610064, People's Republic of China.
Po
P
Yuan
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University , Chengdu 610064, People's Republic of China.
Yanli
Y
Zhang
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University , Chengdu 610064, People's Republic of China.
Xiaochuan
0000-0003-3901-0524
X
Chen
D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry
D001688:Biological Products; D019086:Bridged Bicyclo Compounds, Heterocyclic; D013729:Terpenes; C527915:annuionone B