131685-65-9Relevant academic research and scientific papers
Total synthesis of rutamycin B, a macrolide antibiotic from Streptomyces aureofaciens
White,Hanselmann,Jackson,Porter,Ohba,Tiller,Wang
, p. 5217 - 5231 (2001)
Rutamycin B (2) was synthesized from three principal subunits, spiroketal 75, keto aldehyde 83, and aldehyde 108. First, triol 62 was assembled by Julia coupling of sulfone 56 with aldehyde 58 followed by an acid-catalyzed spiroketalization. The three hydroxyl functions of 62 were successfully differentiated, leading to phosphonate 75. The latter was condensed in a Wadsworth-Emmons reaction with 83, prepared in six steps from (R)-aldehyde 76, to give 92. Coupling of the titanium enolate of 92 with 108 afforded Felkin product 109 with high stereoselectivity in a process that is critically dependent on the presence of the p-methoxybenzyl ether in the aldehyde. Transformation of 109 via aldehyde 116 to vinylboronate 122 was followed by macrocyclization under Suzuki conditions to yield 123. Exhaustive desilylation of the latter yielded rutamycin B.
Assignment of Stereochemistry in the Oligomycin/Rutamycin/Cytovaricin Family of Antibiotics. Asymmetric Synthesis of the Rutamycin Spiroketal Synthon
Evans, David A.,Rieger, Dale L.,Jones, Todd K.,Kaldor, Stephen W.
, p. 6260 - 6268 (2007/10/02)
The absolute stereochemistry of the rutamycin antibiotics 2a,b has been established through asymmetric synthesis of the known degradation product 4.One of the key steps in the assemblage process involves acylation of the metalated hydrazone 6 with the N-m
