title: A chiron approach to the total synthesis of (-)-juglomycin A, (+)-kalafungin, (+)-frenolicin B, and (+)-deoxyfrenolicin.
abstract: A general, efficient, and common strategy for the synthesis of (-)-juglomycin A, (+)-kalafungin, (+)-frenolicin B, and (+)-deoxyfrenolicin is reported here. The strategy involves the synthesis of a key building block alkyne from a cheap chiral pool material, D-glucono-δ-lactone, Dötz benzannulation, oxa-Pictet-Spengler reaction, and H(2)SO(4)-mediated epimerization.
authors.affiliation: Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, Maharashtra, India. rfernand@chem.iitb.ac.in
authors.forename: Rodney A
authors.initials: RA
authors.lastname: Fernandes
authors.forename: Vijay P
authors.initials: VP
authors.lastname: Chavan
authors.forename: Sandip V
authors.initials: SV
authors.lastname: Mulay
authors.forename: Amarender
authors.initials: A
authors.lastname: Manchoju
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D015394:Molecular Structure; D009285:Naphthoquinones / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism; D000095622:Benzoisochromanequinones
chemical_list: D000480:Alkynes; D009285:Naphthoquinones; C018066:frenolicin B; D000095622:Benzoisochromanequinones; C001492:juglomycin; C013079:kalafungin; C004673:deoxyfrenolicin