Total synthesis of cryptophycin 3
Total synthesis of cryptophycin 3
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DOI：
10.1002/ejoc.200400558
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发表时间：
2005-01-14
影响因子：
2.8
通讯作者：
Maier, ME
中科院分区：
文献类型：
--
作者：
Danner, P;Bauer, M;Maier, ME
缩肽念珠藻素3（5）和念珠藻素类似物43由相应的四个亚基制备。三肽类似物34是从含有片段D和C的起始氨基酯33获得的。在通过与羟基酯10的酯化在羧基官能团处进行延伸之后，获得开环化合物37和42。在TBTU作为缩合剂的存在下，通过大环内酰胺化实现闭环。这项工作的特点是一个流线型的合成羟基酯10，一个简短的合成的氨基酸14通过对映选择性烷基化的甘氨酸亚胺21，和使用的Fmoc保护基团的氨基功能。((C)Wiley-VCH Verlag GmbH & Co. KGaA，69451魏因海姆，德国，2005）。
The depsipeptide cryptophycin 3 (5) and the cryptophycin analogue 43 were prepared from the corresponding four sub-units. The tripeptide analogue 34 was acquired from the starting amino ester 33, which contains fragments D and C. After extension at the carboxyl function by esterification with the hydroxy ester 10, the seco compounds 37 and 42 were obtained. Ring closure was achieved by macrolactamization in the presence of TBTU as condensing agent. This work features a streamlined synthesis of the hydroxy ester 10, a short synthesis of the amino acid 14 by enantioselective alkylation of the glycinimine 21, and the use of the Fmoc protecting group for the amino functions. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005).