title: Stereoselective first total synthesis, confirmation of the absolute configuration and bioevaluation of botryolide-E.
abstract: A simple, first stereoselective total synthesis of botryolide-E has been described. The synthesis started from propylene oxide employing Jacobsen's hydrolytic kinetic resolution (HKR), selective epoxide opening, sharpless asymmetric dihydroxylation, one pot acetonide deprotection and lactonization as key steps. Further, the synthesis confirms the absolute configuration of the natural product botryolide-E and we evaluated the biological behavior of natural product botryolide-E against a panel of bacteria and fungi. Botryolide-E exhibits significant potent activity against Staphylococcus aureus (MTCC 96) (6.25 μg/ml), good against Escherichia coli (MTCC 443) (12.5 μg/ml), Bacillus subtilis (MTCC 441) (25 μg/ml) and compound 1 exhibited good to moderate antifungal activity.
authors.affiliation: Natural Products Laboratory, Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad, India.
authors.forename: D Kumar
authors.initials: DK
authors.lastname: Reddy
authors.forename: V
authors.initials: V
authors.lastname: Shekhar
authors.forename: P
authors.initials: P
authors.lastname: Prabhakar
authors.forename: D Chanti
authors.initials: DC
authors.lastname: Babu
authors.forename: D
authors.initials: D
authors.lastname: Ramesh
authors.forename: B
authors.initials: B
authors.lastname: Siddhardha
authors.forename: U S N
authors.initials: US
authors.lastname: Murthy
authors.forename: Y
authors.initials: Y
authors.lastname: Venkateswarlu
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000085:Acetates / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001412:Bacillus subtilis / Q000187:drug effects; D004926:Escherichia coli / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D013211:Staphylococcus aureus / Q000187:drug effects; D013237:Stereoisomerism
chemical_list: D000085:Acetates; D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; C557878:botryolide E; D015107:4-Butyrolactone