ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Synthesis of Macrocyclic α,β-Unsaturated γ-Oxolactones by Ring-Enlargement Reactions; a New Path to the Macrocyclic Lactone Antibiotic A 26771 BA new synthetic route to the α,β-unsaturated γ-oxolactones 2a and 2b, involving two ring-enlarement reactions, is described. Ring opening of bicyclic α-nitroketones of the type 3 gave ring-enlarged compounds of the type 4 which were converted to monoprotected diketones of the type 10 by using a variation of the Nef reaction as a key step. Macrocyclic lactones of the type 11 were obtained by Baeyer-Villiger oxidation and converted into compounds of the type 2. The conversion of 2b to the macrocyclic lactone antibiotic A 26771 B (1) is already described in the literature.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19870700515
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