Synthesis of Tribolure, the Common Aggregation Pheromone of Four Tribolium Flour Beetles
Chao Wang
Department of Medicinal Chemistry, School of Pharmacy, Chinese Pharmaceutical University, Nanjing, Jiangsu 210009, China
Search for more papers by this authorChengyu He
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorCorresponding Author
Yong Shi
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Yong Shi, CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Hua Xiang, Department of Medicinal Chemistry, School of Pharmacy, Chinese Pharmaceutical University, Nanjing, Jiangsu 210009, China
Weisheng Tian, CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorCorresponding Author
Hua Xiang
Department of Medicinal Chemistry, School of Pharmacy, Chinese Pharmaceutical University, Nanjing, Jiangsu 210009, China
Yong Shi, CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Hua Xiang, Department of Medicinal Chemistry, School of Pharmacy, Chinese Pharmaceutical University, Nanjing, Jiangsu 210009, China
Weisheng Tian, CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorCorresponding Author
Weisheng Tian
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Yong Shi, CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Hua Xiang, Department of Medicinal Chemistry, School of Pharmacy, Chinese Pharmaceutical University, Nanjing, Jiangsu 210009, China
Weisheng Tian, CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorChao Wang
Department of Medicinal Chemistry, School of Pharmacy, Chinese Pharmaceutical University, Nanjing, Jiangsu 210009, China
Search for more papers by this authorChengyu He
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorCorresponding Author
Yong Shi
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Yong Shi, CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Hua Xiang, Department of Medicinal Chemistry, School of Pharmacy, Chinese Pharmaceutical University, Nanjing, Jiangsu 210009, China
Weisheng Tian, CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorCorresponding Author
Hua Xiang
Department of Medicinal Chemistry, School of Pharmacy, Chinese Pharmaceutical University, Nanjing, Jiangsu 210009, China
Yong Shi, CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Hua Xiang, Department of Medicinal Chemistry, School of Pharmacy, Chinese Pharmaceutical University, Nanjing, Jiangsu 210009, China
Weisheng Tian, CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorCorresponding Author
Weisheng Tian
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Yong Shi, CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Hua Xiang, Department of Medicinal Chemistry, School of Pharmacy, Chinese Pharmaceutical University, Nanjing, Jiangsu 210009, China
Weisheng Tian, CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorAbstract
Herein we report a synthesis of the natural tribolure, an aggregation pheromone which consists of (4R,8S)-, (4R,8R)-, (4S,8S)-, and (4S,8R)-4,8-dimethyldecanals in a ratio of 4/4/1/1, from (R)-4-methyl-δ-valerolactone, a byproduct of the degradation of steroidal sapogenins. Merging the stereoisomers of the same ratios into one synthetic target and using the same chiron for the construction of the C4 stereocenters are notable features of this synthesis.
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