Total syntheses of lactonamycin and lactonamycin Z with late-stage A-ring formation and glycosylation.

Of Sussex Studies toward a Total Synthesis of Lactonamycin

Dramatic influence of the substitution of alkylidene-5H-furan-2-ones in Diels-Alder cycloadditions with o-quinonedimethide as diene partner: en route to the CDEF polycyclic ring system of lactonamycin.

An efficient and rapid synthesis of the CDEF ring system of lactonamycinone is reported via a highly chemo- and diastereoselective intermolecular Diels-Alder cycloaddition between trans-1,2-disilyloxybenzocyclobutene and the appropriate γ-alkylidenebutenolide. The feasibility and the total chemoselectivity of the [4 + 2] cycloaddition for the construction of a spirolactone moiety via an intramo...

Lactonamycin, a new antimicrobial antibiotic produced by Streptomyces rishiriensis MJ773-88K4. I. Taxonomy, fermentation, isolation, physico-chemical properties and biological activities.

Lactonamycin (1) was isolated from a culture broth of Streptomyces rishiriensis MJ773-88K4. Antibiotic 1 exhibited antimicrobial activities against Gram-positive bacteria including methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant Enterococcus (VRE).

Lactonamycin Z, an antibiotic and antitumor compound produced by Streptomyces sanglieri strain AK 623.

Alkaliphilic streptomycetes strains were included in our HPLC-diode array screening program for detection of novel secondary metabolites. Strain AK 623, which was isolated from a pine wood soil collected at Hamsterley Forest, County Durham, UK, became attractive because of the appearance of a prominent peak in the HPLC chromatogram which did not correspond to any of the 700 reference compounds ...

Total Syntheses of (−)-Kopsifoline D and (−)-Deoxoapodine: Divergent Total Synthesis via Late-Stage Key Strategic Bond Formation

Divergent total syntheses of (-)-kopsifoline D and (-)-deoxoapodine are detailed from a common pentacyclic intermediate 15, enlisting the late-stage formation of two different key strategic bonds (C21-C3 and C21-O-C6) unique to their hexacyclic ring systems that are complementary to its prior use in the total syntheses of kopsinine (C21-C2 bond formation) and (+)-fendleridine (C21-O-C19 bond fo...