title: Formal syntheses of (±)-platensimycin and (±)-platencin via a dual-mode Lewis acid induced cascade cyclization approach.
abstract: A mild and efficient dual-mode Lewis acid induced Diels-Alder (DA)/carbocyclization cascade cyclization reaction has been developed for construction of the tricyclic core of ent-kaurenoids in one pot with the aid of a theoretical study on the π,σ-Lewis acidities of a variety of Lewis acids. With ZnBr2 as the dual-mode Lewis acid, a series of substituted enones and dienes underwent DA/carbocyclization cascade cyclization reaction smoothly at room temperature and provided the tricyclic cyclized products in one pot with good yields and high diastereoselectivity. The tricyclic cyclized product has been successfully utilized as a common intermediate for formal syntheses of (±)-platensimycin and (±)-platencin.
authors.affiliation: Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen University Town, Xili, Shenzhen 518055, China.
authors.forename: Lizhi
authors.initials: L
authors.lastname: Zhu
authors.forename: Congshan
authors.initials: C
authors.lastname: Zhou
authors.forename: Wei
authors.initials: W
authors.lastname: Yang
authors.forename: Shuzhong
authors.initials: S
authors.lastname: He
authors.forename: Gui-Juan
authors.initials: GJ
authors.lastname: Cheng
authors.forename: Xinhao
authors.initials: X
authors.lastname: Zhang
authors.forename: Chi-Sing
authors.initials: CS
authors.lastname: Lee
mesh_terms: D000218:Adamantane / Q000138:chemical synthesis* / Q000737:chemistry; D062365:Aminobenzoates / Q000138:chemical synthesis* / Q000737:chemistry; D000627:Aminophenols / Q000138:chemical synthesis* / Q000737:chemistry; D000813:Anilides / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D058116:Lewis Acids / Q000737:chemistry*; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D062365:Aminobenzoates; D000627:Aminophenols; D000813:Anilides; D058116:Lewis Acids; D011083:Polycyclic Compounds; D000218:Adamantane; C510909:platensimycin; C520340:platencin