title: Studies toward total synthesis of divergolides C and D.
abstract: A facile synthesis of the western segment of divergolides C and D has been developed. Exploratory studies with two disconnections, i.e., C4-C5 vs C5-C6, for elaboration of the ansa bridge to the sterically demanding hexasubstituted naphthalenic aromatic core using a chiral synthon assembled from D-glucose via a stereoselective Johnson orthoester rearrangement is described. The studies set the stage for the completion of the total synthesis of the biologically important novel ansamycins, divergolides C and D, and their structural congeners.
authors.affiliation: Department of Chemistry and Biochemistry, University of Massachusetts Dartmouth, North Dartmouth, Massachusetts 02747, United States. srasapalli@umassd.edu
authors.forename: Sivappa
authors.initials: S
authors.lastname: Rasapalli
authors.forename: Gopalakrishna
authors.initials: G
authors.lastname: Jarugumilli
authors.forename: Gangadhara Rao
authors.initials: GR
authors.lastname: Yarrapothu
authors.forename: James A
authors.initials: JA
authors.lastname: Golen
authors.forename: Arnold L
authors.initials: AL
authors.lastname: Rheingold
mesh_terms: D005947:Glucose / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D017828:Rifabutin / Q000737:chemistry; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry
chemical_list: D018942:Macrolides; C583120:divergolide C; C583119:divergolide D; D017828:Rifabutin; D005947:Glucose