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Stereocontrolled synthesis of a segment having six consecutive chiral centers for the synthesis of erythromycin a from D-glucose

✍ Scribed by Yuji Oikawa; Takao Nishi; Osamu Yonemitsu

Publisher
Elsevier Science
Year
1983
Tongue
French
Weight
222 KB
Volume
24
Category
Article
ISSN
0040-4039

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✦ Synopsis

In order to synthesize erythromycin A from D-glucose as a chiral starting material, the left-hand segment of 9-dihydroerythronolide A having six consecutive chiral centers was synthesized by means of some stereoselective reactions in acyclic systems and MPM protection.

In recent years, much attention has been given to the stereocontrolled synthesis of macrolide and ionophore antibiotics in connection with the establishment of new synthetic methodologies. Stereochemical control in acyclic systems 2) is essential for the total synthesis of such complex molecules other than that in cyclic systems leading to many elegant syntheses of polycyclic compounds such as steroids, alkaloids, terpenes, etc.

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