100905-89-3Relevant articles and documents
A convergent strategy for the pamamycin macrodiolides: Total synthesis of pamamycin-607, pamamycin-593, and pamamycin-621D precursors
Lanners, Steve,Norouzi-Arasi, Hassan,Salom-Roig, Xavier J.,Hanquet, Gilles
, p. 7086 - 7089 (2007)
A convergent total synthesis of pamamycin-607 (1), isolated from Streptomyces alboniger, was achieved by an E-Z isomerization of a tetrahydrofuran alkylidene and a regio- and diastereoselective solvent-dependent cyclo-C6H11BCl/Etsub
Stereoselective synthesis of pamamycin-607
Jeong, Eun Jeong,Kang, Eun Joo,Sung, Lee Taek,Hong, Sung Kil,Lee, Eun
, p. 14655 - 14662 (2007/10/03)
A macrodiolide antibiotic pamamycin-607 was synthesized by joining two hydroxy acid components. Three cis-2, 5-disubstituted tetrahydrofuran rings in the molecule were stereoselectively prepared by radical cyclization reactions of β-alkoxyvinyl ketone intermediates and a β-alkoxymethacrylate substrate. The key step of the synthesis is characterized by the predominant threo product formation in the radical cyclization reaction of a β-alkoxymethacrylate intermediate.
Total synthesis of pamamycin-607
Wang, Yuzhou,Bernsmann, Heiko,Gruner, Margit,Metz, Peter
, p. 7801 - 7804 (2007/10/03)
The macrodiolide antibiotic pamamycin-607 has been synthesized by coupling of the two hydroxy acid constituents using the Yamaguchi method. While the final lactonization with formation of the ester linkage between C(1) and the C(8′) oxygen proceeded with complete C(2) epimerization, the alternative ring closure involving the carboxylic acid of the smaller fragment and the hydroxyl group of the larger fragment yielded the target molecule.