title: Synthetic studies toward sarain A. Formation of the western macrocyclic ring.
abstract: Starting with the tricyclic core 2b, annulation to form the 13-membered western ring of sarain A has been achieved to afford the macrocycle 30a by initial construction of the sterically congested quaternary center at C-3, followed by elaboration of the C-3 side-chain and ring-closing olefin metathesis. Also included is a parallel conversion of tricycle 2c to macrocycle 30b containing a functionalized side-chain at N-1 suitable for attachment of the eastern macrocyclic ring.
authors.affiliation: Department of Chemistry, University of Alabama, Tuscaloosa, Alabama 35487, USA.
authors.forename: Moo Je
authors.initials: MJ
authors.lastname: Sung
authors.forename: Hyoung Ik
authors.initials: HI
authors.lastname: Lee
authors.forename: Hee Bong
authors.initials: HB
authors.lastname: Lee
authors.forename: Jin Kun
authors.initials: JK
authors.lastname: Cha
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis*; D000818:Animals; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis*; D002384:Catalysis; D003500:Cyclization; D007202:Indicators and Reagents; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011084:Polycyclic Aromatic Hydrocarbons / Q000138:chemical synthesis*; D011161:Porifera / Q000737:chemistry; D013329:Structure-Activity Relationship
chemical_list: D000470:Alkaloids; D001952:Bridged-Ring Compounds; D007202:Indicators and Reagents; D011084:Polycyclic Aromatic Hydrocarbons; C410431:sarain A