title: Catalytic Asymmetric Total Synthesis of Hedyosumins A, B, and C.
abstract: The first and asymmetric total synthesis of hedyosumins A, B, and C was accomplished in 13-14 steps from simple starting materials. The essential tools that allow us to access the tetracyclic skeleton include an organocatalytic [4 + 3] cycloaddition reaction, an intramolecular aldol condensation, and an intramolecular carboxymercuration/demercuration enabled lactonization. A CBS-catalyzed asymmetric reduction was employed to boost the ee of the synthetic natural products to an excellent level. This synthesis established the absolute configurations of hedyosumins A, B, and C.
authors.affiliation: CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry , 345 Lingling Road, Shanghai 200032, China.|Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry and Chemical Engineering, Soochow University , Suzhou, Jiangsu 215123, China.
authors.forename: Wang-Bin
authors.initials: WB
authors.lastname: Sun
authors.affiliation: CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry , 345 Lingling Road, Shanghai 200032, China.
authors.forename: Xuan
authors.initials: X
authors.lastname: Wang
authors.affiliation: CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry , 345 Lingling Road, Shanghai 200032, China.
authors.forename: Bing-Feng
authors.initials: BF
authors.lastname: Sun
authors.affiliation: Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry and Chemical Engineering, Soochow University , Suzhou, Jiangsu 215123, China.
authors.forename: Jian-Ping
authors.initials: JP
authors.lastname: Zou
authors.affiliation: CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry , 345 Lingling Road, Shanghai 200032, China.
authors.forename: Guo-Qiang
authors.initials: GQ
authors.lastname: Lin
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D018360:Crystallography, X-Ray; D004365:Drugs, Chinese Herbal / Q000138:chemical synthesis* / Q000737:chemistry; D019684:Magnoliopsida / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure; D045789:Sesquiterpenes, Guaiane / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000447:Aldehydes; D001688:Biological Products; D004365:Drugs, Chinese Herbal; D045789:Sesquiterpenes, Guaiane; C000609310:hedyosumin A; C000609311:hedyosumin B; C000609312:hedyosumin C; C116609:3-hydroxybutanal