title: Unified strategy for the synthesis of the "miscellaneous" lycopodium alkaloids: total synthesis of (+/-)-lyconadin A.
abstract: Total synthesis of the Lycopodium alkaloid lyconadin A was achieved in 18 steps starting from a readily available vinylogous ester and bromopicoline. The key step in the total synthesis is a proximity-driven oxidative C-N bond-forming reaction that yields the lyconadin pentacycle from a tetracyclic precursor. The key tetracycle, which has been prepared for the first time, is a versatile intermediate that may be utilized for the total synthesis of a variety of Lycopodium alkaloids. Critical to the success of this plan was the efficient preparation of a pyridine-annulated cycloheptadiene tricycle that promises to be a general strategy to access a variety of seven-membered ring containing natural products.
authors.affiliation: Department of Chemistry, University of California, Berkeley, California 94720, USA.
authors.forename: Alakesh
authors.initials: A
authors.lastname: Bisai
authors.forename: Scott P
authors.initials: SP
authors.lastname: West
authors.forename: Richmond
authors.initials: R
authors.lastname: Sarpong
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis*; D011083:Polycyclic Compounds / Q000138:chemical synthesis*
chemical_list: D000470:Alkaloids; D011083:Polycyclic Compounds; C435307:lyconadin A