190912-17-5Relevant articles and documents
Total Synthesis of Mycinamicin IV as Integral Part of a Collective Approach to Macrolide Antibiotics
Sp?th, Georg,Fürstner, Alois
, (2022/01/13)
The total synthesis of the 16-membered macrolide mycinamicin IV is outlined, which complements our previously disclosed, largely catalysis-based route to the aglycone. This work must also be seen in the context of our recent conquest of aldgamycin N, a related antibiotic featuring a similar core but a distinctly different functionalization pattern. Taken together, these projects prove that the underlying blueprint is integrative and hence qualifies for a collective approach to this prominent class of natural products. In both cases, the final glycosylation phase mandated close attention and was accomplished only after robust de novo syntheses of the (di)deoxy sugars of the desosamine, chalcose, mycinose and aldgarose types had been established. Systematic screening of the glycosidation promoter was also critically important for success.
A Scalable Synthesis of (R,R)-2,6-Dimethyldihydro-2H-pyran-4(3H)-one
Young, Ian S.,Haley, Matthew W.,Tam, Annie,Tymonko, Steven A.,Xu, Zhongmin,Hanson, Ronald L.,Goswami, Animesh
, p. 1360 - 1368 (2015/11/02)
A scalable synthesis of (R,R)-2,6-dimethyldihydro-2H-pyran-4(3H)-one is reported. Key to this strategy is the Ti(OiPr)4-catalyzed Kulinkovich cyclopropanation of silyl protected (R)-ethyl 3-hydroxybutanoate, and subsequent oxidative fragmentati