Synthetic studies toward sarain A. Formation of the western macrocyclic ring.
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.
Sung
Moo Je
MJ
Department of Chemistry, University of Alabama, Tuscaloosa, Alabama 35487, USA.
Lee
Hyoung Ik
HI
Lee
Hee Bong
HB
Cha
Jin Kun
JK
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
D000470:Alkaloids; D001952:Bridged-Ring Compounds; D007202:Indicators and Reagents; D011084:Polycyclic Aromatic Hydrocarbons; C410431:sarain A