Total asymmetric synthesis of the potent immunosuppressive marine natural product microcolin A
Total asymmetric synthesis of the potent immunosuppressive marine natural product microcolin A
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DOI：
10.1021/jo952123l
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发表时间：
1996-05-17
影响因子：
3.6
通讯作者：
Grover, P
中科院分区：
文献类型：
--
作者：
Decicco, CP;Grover, P
本文报道了免疫抑制化合物Microcolin A的全不对称合成。该合成建立了Microcolin A的绝对立体化学为C-36 R、C-38 R和C-4S，其基础是从天然L-（S）-丙氨酸出发，非对映选择性地制备了脂质区的所有四种可能的非对映体（片段A）和非对映选择性地合成片段C。该策略涉及三个光学纯片段的会聚组装，并且可以进行化学修饰以检查用于生物学研究的结构类似物。
The total asymmetric synthesis of the potent immunosuppressive compound microcolin A is reported, The synthesis establishes the absolute stereochemistry of microcolin A as C-36R, C-38R, and C-4S on the basis of the diastereoselective preparation of all four possible diastereomers of the lipid region (fragment A) and diastereoselective synthesis of fragment C starting from natural L-(S)-alanine. The strategy involves a convergent assemblage of three optically pure fragments and is amenable to chemical modifications to examine structural analogs for biological study.