Synthetic studies of erythromycins. II. Enantiospecific synthesis of A C-10-C-13 segment of erythronolide a from D-ribose
β Scribed by Mitsuhiro Kinoshita; Masayuki Arai; Katsuhiko Tomooka; Masaya Nakata
- Publisher
- Elsevier Science
- Year
- 1986
- Tongue
- French
- Weight
- 266 KB
- Volume
- 27
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
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 recently been achieved by two Harvard groups, 2,3 one of which succeeded during the final stages of their conquest of erythromycin A itself.
3 Other synthetic efforts have been announced. 4
In the studies
π SIMILAR VOLUMES
The preparation of t3C-labeled ribonucleosides starting from D-[t3C~]glucose in 45% overall yield is described. The key of this short synthetic way is the dehomologation of di-O-isopropylidene hexofuranose 2 with periodic acid and NaBI-I4 that afforded stereoselectively the labeled ribofuranose deri