An improved asymmetric synthesis of malyngamide U and its 2'-epimer.
An accelerated and improved asymmetric synthesis of malyngamide U (1) and its 2'-epimer (2'-epi-1) was accomplished from readily available n-hexanal, ethanolamine and (R)-(-)-carvone. The key steps involved a Johnson-Claisen rearrangement in the synthesis of an unsaturated carboxylic acid 4 and an aldol reaction in the construction of the skeleton of 1 and 2'-epi-1. There are 13 steps in the synthesis, with a 2.7% overall yield for 1 and a 0.4% yield for 2'-epi-1.
Feng
Jian-Peng
JP
State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000, PR China.
Shi
Zi-Fa
ZF
Li
Yang
Y
Zhang
Jun-Tao
JT
Qi
Xian-Liang
XL
Chen
Jie
J
Cao
Xiao-Ping
XP
D000438:Alcohols / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D000081005:Cyclohexane Monoterpenes; D003512:Cyclohexanones / Q000138:chemical synthesis*; D019856:Ethanolamine / Q000737:chemistry*; D005229:Fatty Acids, Monounsaturated / Q000138:chemical synthesis*; D008956:Models, Chemical; D039821:Monoterpenes / Q000737:chemistry*
D000438:Alcohols; D000447:Aldehydes; D002264:Carboxylic Acids; D000081005:Cyclohexane Monoterpenes; D003512:Cyclohexanones; D005229:Fatty Acids, Monounsaturated; D039821:Monoterpenes; C474704:malyngamide U; D019856:Ethanolamine; C006923:carvone; C010463:n-hexanal