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Synthesis of 16-membered ring macrolide antibiotics I. Stereoselective construction of the ‘right wing” of the carbomycins and leucomycins from D-glucose

✍ Scribed by K.C. Nicolaou; M.R. Pavia; S.P. Seitz

Publisher
Elsevier Science
Year
1979
Tongue
French
Weight
227 KB
Volume
20
Category
Article
ISSN
0040-4039

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✦ Synopsis

D-Glucose was converted to a backbone chain containing the appropriate functionalities an correc7 stereochemistry for the construction of the Cl-C9 fragment of the 16-membered ring macrolide antibiotics carknycin A and B and leuccqzin A3. Ieucctnycin AS and carkmycins A and B (magnamycins A and B) shown below are members of the clinically important 16-membered ring class of macrolide antibiotics.

1 We wish to report a highly efficient synthesis of the "right wing" segment (Cl-C9) of these substances fran "glu-.

case. ckr synthetic plan called for the construction of the Michael acceptor 2 (Scheme I) corresponding to the Cl-C6 fragment of these 1 6-membered ring macrolides. The cr,@-unsaturated ester 6 was then to be utilized for building up the complete "right wing" (Cl-a) as the aldehyde 2, onto which the "left wing" will be attached. Both the construction of 5 and the successful 1,4 addition of cuprate reagents to this acceptor have now been realized and are reported herein. LEUCOMYCIN A, CARBOMYClN B CARBOMYCIN A

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