A unified synthetic approach to polyketides having both skeletal and stereochemical diversity.
An efficient systematic approach to the diversity-oriented synthesis of polyketides has been developed to provide both skeletal and stereochemical diversity. Each synthetic intermediate is also a desired polyketide fragment and no protecting group manipulations are required. A first-generation synthesis provides a 74-membered polyketide library comprising six different skeletal classes, each in one to five steps from propargylic alcohol precursors. A study of epoxyol opening reactions revealed unusual reactivity trends based on epoxide configuration.
Shang
Shiying
S
Pharmacology Program, Weill Graduate School of Medical Sciences of Cornell University, Memorial Sloan-Kettering Cancer Center, New York, NY 10021, USA.
Iwadare
Hayato
H
Macks
Daniel E
DE
Ambrosini
Lisa M
LM
Tan
Derek S
DS
D002244:Carbon / Q000737:chemistry; D004852:Epoxy Compounds / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry*; D008745:Methylation; D015394:Molecular Structure; D013237:Stereoisomerism
D004852:Epoxy Compounds; D018942:Macrolides; D002244:Carbon