title: A bifunctional Lewis acid induced cascade cyclization to the tricyclic core of ent-kaurenoids and its application to the formal synthesis of (±)-platensimycin.
abstract: A mild and efficient bifunctional Lewis acid induced cascade cyclization reaction has been developed for construction of the tricyclic core of ent-kaurenoids. With ZnBr(2) as the bifunctional Lewis acid, a series of substituted enones and dienes underwent cascade cyclization smoothly at room temperature and provided the tricyclic products in one pot with good yields (75-91%) and high diastereoselectivity. The cyclized product has been successfully employed for the formal synthesis of (±)-platensimycin.
authors: Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen University Town, Xili, Shenzhen 518055, China.
authors: Lizhi
authors: L
authors: Zhu
authors: Yejian
authors: Y
authors: Han
authors: Guangyan
authors: G
authors: Du
authors: Chi-Sing
authors: CS
authors: Lee
mesh_terms: D000218:Adamantane / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D062365:Aminobenzoates / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000813:Anilides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000929:Antidepressive Agents, Tricyclic; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D045786:Diterpenes, Kaurane / Q000737:chemistry*; D058116:Lewis Acids / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D062365:Aminobenzoates; D000813:Anilides; D000929:Antidepressive Agents, Tricyclic; D045786:Diterpenes, Kaurane; D058116:Lewis Acids; D000218:Adamantane; C510909:platensimycin