Synthesis of the Fully Functionalized Core Structure of the Antibiotic Abyssomicin C

Abstract

[reaction: see text] The fully functionalized core structure 23 of abyssomicin C (6) containing an oxabicyclooctane ring and a tetronate was prepared via a Diels-Alder approach. After hydroxylation of lactone 10 to the alpha-hydroxylactone 12, lactone opening led to the hydroxy ester 16. A directed epoxidation furnished the desired syn-epoxide 20. Acetylation of the tertiary hydroxyl group, followed by intramolecular Claisen condensation, gave directly the core structure 23.

Gut bacteria of cockroaches are a potential source of antibacterial compound(s)

“…The Actinobacteria (family Actinomycetaceae ) produced numerous secondary metabolites active against pathogens (Rath et al . ). Secondary metabolites from marine Actinobacteria are structurally diverse and show unique biological activities against bacteria, fungi, viruses and parasites (Manivasagan et al .…”

Transition metals in organic synthesis: Highlights for the year 2005

“…Synthetic targets include, tetracyclic core of ingenol [1509], epoxyquinols A-C and epoxytwinol A [212], 1-deoxypaclitaxel precursor [1510], ovalicin [1144], polar core of scyphostatin [1511], abyssomicin C [1512] and ABCD ring of gambierol [1513]. A molybdenum catalyzed epoxidation was used in a synthesis of (+)-apiosporamide (Eq.…”

Antimicrobial Activity of the Crude Extract Derived from Streptomyces spp. Associated with Sponges

“…In the present study it was observed that the crude extract inhibited the growth of both gram positive and gram negative bacteria. Similarly Basilio et al, (2003), and Rath et al, (2005), also reported the inhibitory effect of ethyl acetate extract of Streptomyces sp. on both gram positive and gram negative bacteria.…”