A stereoselective synthesis of (+)-herboxidiene/GEX1A.
A stereoselective synthesis of (+)-herboxidiene is described. The convergent synthesis utilized a Suzuki cross-coupling reaction to assemble the key segments. The synthesis of the functionalized tetrahydropyran ring utilized an Achmatowicz reaction as the key step. The synthesis of the C10-C19 segment was accomplished using Brown's crotylboration, asymmetric alkylation, and a stereoselective allylic chlorination reactions.
Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907, United States. akghosh@purdue.edu
Arun K
AK
Ghosh
Jianfeng
J
Li
D001897:Boronic Acids / Q000737:chemistry; D005233:Fatty Alcohols / Q000138:chemical synthesis*; D054879:Halogenation; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis*; D013237:Stereoisomerism
D001897:Boronic Acids; D005233:Fatty Alcohols; D011714:Pyrans; C076087:herboxidiene