Total synthesis of aigialomycin D.
[reaction: see text] The first total synthesis of resorcinylic macrolide aigialomycin D was described. The resorcinylic moiety was constructed by a highly efficient Diels-Alder reaction using a disiloxydiene and a 14-membered "ynolide" as the dienophile synthesized by ring-forming olefin metathesis.
Geng
Xudong
X
Laboratory for Bioorganic Chemistry, Sloan-Kettering Institute for Cancer Research, 1275 York Avenue, New York, New York 10021, USA.
Danishefsky
Samuel J
SJ
D003521:Cyclopropanes / Q000737:chemistry; D007783:Lactones / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D003521:Cyclopropanes; D007783:Lactones; D018942:Macrolides; C452445:aigialomycin D; C477936:cycloproparadicicol; C035359:monorden