Synthesis of the C1-C9 fragment of callipeltoside-A.
[reaction: see text] The C1-C9 fragment of callipeltoside (17) was prepared in 12 steps and 7.2% overall yield from bicyclic lactone (+)-4. Key steps include a stereoselective epoxidation and further regiocontrolled nucleophilic opening of the oxirane ring to install two vicinal stereocenters (C5 and C6), and the use of bis(trimethylsilyl) peroxide and a catalytic amount of Sn(IV) chloride for the chemoselective Baeyer-Villiger oxidation of unsaturated cyclopentanone 15.
Velázquez
F
F
Division of Medicinal and Natural Products Chemistry, College of Pharmacy, and The Center for Biocatalysis and Bioprocessing, The University of Iowa, Iowa City, Iowa 52242, USA.
Olivo
H F
HF
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D001671:Biochemistry / Q000379:methods*; D018942:Macrolides
D000900:Anti-Bacterial Agents; D018942:Macrolides; C410329:callipeltoside A