CHIRAL SYNTHESIS OF POLYKETIDE-DERIVED NATURAL-PRODUCTS .4. SYNTHESIS OF A LEFT-HAND SEGMENT WITH 6 CONSECUTIVE CHIRAL CENTERS OF DIHYDROERYTHRONOLIDE-A FOR THE TOTAL SYNTHESIS OF ERYTHROMYCIN-A FROM D-GLUCOSE
CHIRAL SYNTHESIS OF POLYKETIDE-DERIVED NATURAL-PRODUCTS .4. SYNTHESIS OF A LEFT-HAND SEGMENT WITH 6 CONSECUTIVE CHIRAL CENTERS OF DIHYDROERYTHRONOLIDE-A FOR THE TOTAL SYNTHESIS OF ERYTHROMYCIN-A FROM D-GLUCOSE
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DOI：
10.1039/p19850000007
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发表时间：
1985-01-01
期刊：
影响因子：
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通讯作者：
YONEMITSU, O
中科院分区：
文献类型：
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作者：
OIKAWA, Y;NISHI, T;YONEMITSU, O
为了从 D-葡萄糖全合成红霉素 A [一种抗生素]，借助无环系统中的立体化学控制和对甲氧基苯甲基 (MPM) 保护，(2R,3S,4S,5R,6R,7R)-1-羟基-5,6-异丙叉二氧基-3,7-双(4-甲氧基苄氧基)-2,4,6-三甲基壬烷，左侧片段对应9-二氢赤酮内酯A的C-7-C-15片段是由(2)通过开链系统中的一些立体选择性反应合成的，例如Wittig反应、OsO4氧化和环氧化。
For the purpose of the total synthesis of erythromycin A [an antibiotic] from D-glucose with the aid of stereochemical control in acyclic systems and p-methoxyphenylmethyl (MPM) protection, (2R,3S,4S,5R,6R,7R)-1-hydroxy-5,6-isopropylidenedioxy-3,7-bis(4-methoxybenzyloxy)-2,4,6-trimethylnonane, a left-hand segment corresponding to the C-7-C-15 segment of 9-dihydroerythronolide A, was synthesized from (2) through some stereoselective reactions in open-chain systems, e.g., the Wittig reaction, OsO4 oxidation and epoxidation.