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Macrolide antibiotic (-)-A26771B

Total synthesis of 16 membered Makrolid Antibiotika (-)-A26771B

The preparation of macrolides has received much attention due to their challenging structures and high biological activities. The key step of our synthesis was a macrolactonization strategy leading to a 16-membered ring. The thermal cycloreversion of dioxolenones followed by intramolecular ketene trapping constitutes a rather unexplored means for this conversion. Another key step was the introduction of the trans-diol moiety by Sharpless AD-methodology.

In summary an asymmetric synthesis of (-)-A26771B in 11 steps from commercially available (R)-methyloxirane with an overall yield of 17 % has been described.

J. Gebauer, S. Blechert, Synthesis of b,g-unsaturated-b-keto Lactones via Sequential Cross Metathesis-Lactonization: A Facile Entry to Macrolide Antibiotic (-)-A26771B, J. Org. Chem. 2006, 71, 2021-2025. [DOI]

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