NEW AND EFFICIENT APPROACHES TO THE SEMISYNTHESIS OF TAXOL AND ITS C-13 SIDE-CHAIN ANALOGS BY MEANS OF BETA-LACTAM SYNTHON METHOD
NEW AND EFFICIENT APPROACHES TO THE SEMISYNTHESIS OF TAXOL AND ITS C-13 SIDE-CHAIN ANALOGS BY MEANS OF BETA-LACTAM SYNTHON METHOD
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DOI：
10.1016/s0040-4020(01)91210-4
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发表时间：
1992-08-21
期刊：
影响因子：
2.1
通讯作者：
BRIGAUD, T
中科院分区：
文献类型：
--
作者：
OJIMA, I;HABUS, I;BRIGAUD, T
通过高效的手性烯醇化酯-亚胺缩合反应，合成了对映体纯度高的3-羟基-4-芳基-β-内酰胺类化合物，并成功地应用于紫杉醇C-13侧链N-苯甲酰基-（2 R，3S）-3-苯基-异丝氨酸及其类似物的不对称合成。(3R容易从3-羟基-4-苯基-β-内酰胺衍生的N-苯甲酰基-3-（1-乙氧基乙氧基）-4-苯基-2-氮杂环丁酮与被保护的浆果赤霉素III偶联，然后脱保护，以良好的产率得到光学纯的紫杉醇和10-脱乙酰基-7，10-双（Troc）-紫杉醇。完全指定的H-1，C-13，和2D（COSY和HETCOR）NMR光谱的紫杉醇合成的显示和讨论。
Highly efficient chiral ester enolate-imine condensation giving 3-hydroxy-4-aryl-beta-lactams with excellent enantiomeric purity is successfully applied to the asymmetric synthesis of the enantiomerically pure taxol C-13 side chain, N-benzoyl-(2R,3S)-3-phenyl-isoserine and its analogs. (3R,4S)-N-benzoyl-3-(1-ethoxyethoxy)-4-phenyl-2-azetidinone readily derived from the 3-hydroxy-4-phenyl-beta-lactam is coupled with protected baccatin IIIs, followed by deprotection to give optically pure taxol and 10-deacetyl-7,10-bis(Troc)-taxol in good yields. Fully assigned H-1, C-13, and 2D (COSY and HETCOR) NMR spectra of taxol thus synthesized are shown and discussed.