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Synthetic studies of erythromycins. III. Total synthesis of erythronolide a through (9s)-9-dihydroerythronolide A

✍ Scribed by Mitsuhiro Kinoshita; Masayuki Arai; Naoki Ohsawa; Masaya Nakata

Publisher
Elsevier Science
Year
1986
Tongue
French
Weight
265 KB
Volume
27
Category
Article
ISSN
0040-4039

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A rather facile stereoselective total synthesis of (9S)-9-dihydroerythronolide A starting from D-glucose was achieved via coupling of Cl-C6 and C7-Cl5 segments and subsequent macrolactonizotion. The well known macrolide antibiotic erythromycin A (1) has been an attractive synthetic target for moder

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3, a C-10-C-13 synthetic segment of erythronolide A (lJ was enantiospecifically synthesized in sixteen steps and 8.3% overall yield from D-ribose. The successful total synthesis of erythronolide A (A), aglycone of the medicinally important 14-membered macrolide antibiotic erythromycin A, has recent