An Efficient Multigram Synthesis of Alkannin and Shikonin
An Efficient Multigram Synthesis of Alkannin and Shikonin
复制标题
阿尔坎宁和紫草素的高效多克合成
DOI：
10.1002/ejoc.201101505
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发表时间：
2012-03-01
影响因子：
2.8
通讯作者：
Li, Shaoshun
中科院分区：
文献类型：
--
作者：
Wang, Rubing;Zhou, Shanshan;Li, Shaoshun
通过对一个关键的酸性中间体的拆分，实现了紫草素（1）和紫草素（2）的全合成，总收率99% ee，15.6？% 1和99.8% ee，11.9%对于2）。该合成策略的关键步骤包括方便地合成和分离一对酰胺非对映异构体，温和水解酰胺以除去胺手性助剂，以及有效的甲基保护基脱保护序列。
The concise and efficient total syntheses of alkannin (1) and shikonin (2), based on the resolution of a key acid intermediate, are achieved with excellent enantiomeric excesses and high overall yields (99?% ee, 15.6?% for 1 and 99.8?% ee, 11.9?% for 2). The key steps of the synthetic strategy involve the convenient synthesis and separation of a pair of amide diastereoisomers and the mild hydrolysis of the amide to remove the amine chiral auxiliary, together with an efficient deprotection sequence of the methyl protecting groups.