Enantioselective total synthesis of phomallenic acid C.
The newly isolated bacterial FAS II inhibitor phomallenic acid C (3) was synthesized for the first time as a 16:1 mixture of the (R)- and (S)-isomer with the diyne-allene motif constructed using a coupling under Negishi conditions. By comparison with the synthetic sample, the natural phomallenic acid C was estimated to be a 3.8:1 mixture of (R)-/(S)-isomers. This synthesis describes a new synthetic entry to optically active allene diynes.
Jian
Ya-Jun
YJ
State Key Laboratory of Bioorganic And Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China.
Tang
Chao-Jun
CJ
Wu
Yikang
Y
D000466:Alkadienes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000466:Alkadienes; C509901:phomallenic acid C