TOTAL SYNTHESIS OF THE ANTHELMINTIC MACROLIDE AVERMECTIN B1A
TOTAL SYNTHESIS OF THE ANTHELMINTIC MACROLIDE AVERMECTIN B1A
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DOI：
10.1039/p19910000667
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发表时间：
1991-04-01
期刊：
影响因子：
--
通讯作者：
WOODS, M
中科院分区：
文献类型：
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作者：
LEY, SV;ARMSTRONG, A;WOODS, M
报道了驱虫药阿维菌素B1 a-1的全合成方法。 该合成的关键特征包括通过对称的1，4-双-环氧化物4的选择性开环引入C（11）-C（15）部分，然后与衍生自3-甲基-2-（1-甲基丙基）-6-苯磺酰基吡喃3的阴离子反应，得到“北方”C（11）-C（25）片段39。 衍生的C（11）-C（25）醛单元42与C（1）-C（10）“southern”片段2的偶联通过新的解偶联乙烯基砜阴离子序列实现。 大环内酯化和随后引入3，4-双键得到糖苷配基部分51。 通过5-乙酰化糖苷配基70和硫代羰基咪唑69之间的新型银介导的偶联引入oleandrosyloleandrose二糖。 使用Super-Hydride完成最终脱乙酰化，得到天然产物1。
A highly convergent total synthesis of the anthelmintic macrolide avermectin B1a 1 is described. The key features of this synthesis include the introduction of the C(11)-C(15) portion by selective ring opening of a symmetrical 1,4-bis-epoxide 4 followed by reaction with the anion derived from the 3-methyl-2-(1-methylpropyl)-6-phenylsulphonylpyran 3 to afford the 'northern' C(11)-C(25) fragment 39. Coupling of the derived C(11)-C(25) aldehyde unit 42 with a C(1)-C(10) 'southern' fragment 2 was achieved via a novel deconjugative vinyl sulphone anion sequence. Macrolactonisation and subsequent introduction of the 3,4-double bond gave the aglycone portion 51. The oleandrosyloleandrose disaccharide was introduced by a novel silver-mediated coupling between the 5-acetylated aglycone 70 and the thiocarbonylimidazolide 69. Final deacetylation was accomplished using Super-Hydride to give the natural product 1.