Stereocontrolled synthesis of the DE ring system of the marine alkaloid upenamide.
[reaction: see text] A stereocontrolled synthesis of the DE fragment (2) of the marine alkaloid upenamide (1) is described. The synthesis proceeds in 12 steps from caprolactone (10) and 20-25% overall yield.
Kiewel
Kurt
K
Department of Chemistry, Texas A&M University, College Station, Texas 77842-3012, USA.
Luo
Zhushou
Z
Sulikowski
Gary A
GA
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D000818:Animals; D002208:Caproates / Q000737:chemistry*; D007783:Lactones / Q000737:chemistry*; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry; D011807:Quinolizines / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D002208:Caproates; D007783:Lactones; D011807:Quinolizines; D013141:Spiro Compounds; C418125:upenamide; C121056:caprolactone