A highly E-stereoselective approach to beta-iodo Morita-Baylis-Hillman esters: synthesis of secokotomolide A.
A geometric-selective synthesis of (E)-beta-iodo Morita-Baylis-Hillman esters has been developed through a three-component aldol-type reaction using BF3.Et2O and TMS-I. The synthetic utility of the (E)-beta-iodo Morita-Baylis-Hillman esters was demonstrated in the first reported short synthesis of secokotomolide A.
Lee
Sung Il
SI
Department of Chemistry, Sungkyunkwan University, Suwon 440-746, Korea Gyeonggi Science High School, Suwon, Korea.
Hwang
Geum-Sook
GS
Shin
Su Cheol
SC
Lee
Tae Gyo
TG
Jo
Ran Hee
RH
Ryu
Do Hyun
DH
D000447:Aldehydes / Q000737:chemistry; D000473:Alkanes / Q000138:chemical synthesis* / Q000737:chemistry; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D000447:Aldehydes; D000473:Alkanes; D004952:Esters; C525796:secokotomolide A