Total synthesis of aigialomycin D using a Ramberg-Bäcklund/RCM strategy.
The bioactive resorcylic acid lactone aigialomycin D (1) has been synthesized by a novel combination of ring-closing metathesis (RCM) and Ramberg-Bäcklund reactions. This synthetic strategy enables the C1'-C2' alkene to be masked as a sulfone during formation of the macrocycle by ring closing metathesis at the C7'-C8' olefin, thus avoiding competing formation of a cyclohexene. A subsequent Ramberg-Bäcklund reaction efficiently produces the C1'-C2' E-alkene. This combined RCM/Ramberg-Bäcklund reaction strategy should be widely applicable to the synthesis of macrocyclic dienes.
Baird
Lynton J
LJ
School of Chemical and Physical Sciences, Centre for Biodiscovery, Victoria University of Wellington, P.O. Box 600, Wellington, New Zealand.
Timmer
Mattie S M
MS
Teesdale-Spittle
Paul H
PH
Harvey
Joanne E
JE
D000475:Alkenes / Q000737:chemistry; D003500:Cyclization; D007783:Lactones / Q000737:chemistry; D047028:Macrocyclic Compounds / Q000138:chemical synthesis; D018942:Macrolides / Q000138:chemical synthesis*; D013450:Sulfones / Q000737:chemistry
D000475:Alkenes; D007783:Lactones; D047028:Macrocyclic Compounds; D018942:Macrolides; D013450:Sulfones; C452445:aigialomycin D