The first total synthesis of 15-deoxy-Delta12,14-prostaglandin J2 and the unambiguous assignment of the C14 stereochemistry.
[reaction: see text] The first total synthesis of 15-deoxy-Delta12,14-prostaglandin J2 is reported. The highly unsaturated cyclopentenone prostaglandin was obtained via a silicon-tethered allenic [2 + 2 + 1] cycloaddition reaction developed in our group. In addition, the stereochemistry at C14 has been assigned unambiguously.
Brummond
Kay M
KM
University of Pittsburgh, Department of Chemistry, Pittsburgh, Pennsylvania 15260, USA. kbrummon@pitt.edu
Sill
Peter C
PC
Chen
Hongfeng
H
D002244:Carbon / Q000737:chemistry; D003500:Cyclization; D015394:Molecular Structure; D015230:Prostaglandin D2 / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D012825:Silicon / Q000737:chemistry; D013237:Stereoisomerism
C477819:15-deoxyprostaglandin J2; D002244:Carbon; D015230:Prostaglandin D2; D012825:Silicon