Novel synthesis of the ABC rings of solanoeclepin A.
A stereocontrolled synthesis of the ABC rings of solanoeclepin A has been achieved. The seven-membered ring B was synthesized by an intramolecular Prins-ene reaction between an aldehyde and an enyne-dicobalthexacarbonyl complex. The acetylene in this synthesis plays multiple roles: to join the A and C rings, to allow stereoselective cyclization via dicobalthexacarbonyl complexation, and to facilitate Nicholas cation stabilization followed by deprotonation to form an endo-cyclic olefin (Nicholas-Prins cyclization).
Department of Chemistry, National Tsing Hua University , 101, Section 2, Kuang-Fu Road, Hsinchu 30013, Taiwan.
Ya-Ting
YT
Lin
Feng-Yi
FY
Lin
Minoru
M
Isobe
D000447:Aldehydes / Q000737:chemistry; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D006586:Hexanes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000447:Aldehydes; D001952:Bridged-Ring Compounds; D006586:Hexanes; C431673:solanoeclepin A