Total synthesis of cyclic tetrapeptide FR235222, a potent immunosuppressant that inhibits mammalian histone deacetylases

被引:56
作者
Xie, WQ
Zou, B
Pei, DQ
Ma, DW
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China
[2] Univ Minnesota, Dept Pharmacol, Minneapolis, MN 55455 USA
关键词
D O I
10.1021/ol050991r
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
yThe 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.
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页码:2775 / 2777
页数:3
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