Xie Weiqing, Zou Bin, Pei Duanqing, Ma Dawei
State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.
Org Lett. 2005 Jun 23;7(13):2775-7. doi: 10.1021/ol050991r.
[structure: see text] The total synthesis of FR235222, a potent immunosuppressant with in vivo activities, has been achieved. The key steps include assembling its (2S,9R)-2-amino-9-hydroxy-8-oxodecanoic acid residue via an olefin cross-metathesis of a methyl (R)-lactate-derived homoallyl ketone with protected allyl amino acid and constructing its trans-(2R,4S)-4-methylproline unit from protected (R)-pyroglutamic acid in seven steps.
[结构：见正文] 具有体内活性的强效免疫抑制剂FR235222已实现全合成。关键步骤包括通过（R）-乳酸甲酯衍生的高烯丙基酮与受保护的烯丙基氨基酸进行烯烃交叉复分解反应来组装其（2S，9R）-2-氨基-9-羟基-8-氧代癸酸残基，并从受保护的（R）-焦谷氨酸经七步构建其反式-（2R，4S）-4-甲基脯氨酸单元。
