First total synthesis of the marine natural products clavulolactones II and III.
The first total synthesis of the marine prostanoids clavulolactones II and III is presented from an easily accessible chiral, non-racemic cyclopentenone intermediate. Key steps involve selective TBDMS deprotection, selective reduction of the β-side chain and aldol condensation. Clavulolactones II and III were successfully prepared from (S)-4-((tert-butyldimethylsilyl)oxy) cyclopent-2-en-1-one over nine steps, in overall yields of 21 and 7% respectively.
Department of Chemistry, University of Oslo, Blindern, 0315 Oslo, Norway. tore.benneche@kjemi.uio.no.
Charlotte M
CM
Miller
Tore
T
Benneche
Marcus A
MA
Tius
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry; D009792:Oceans and Seas; D011453:Prostaglandins / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D001688:Biological Products; D003517:Cyclopentanes; D011453:Prostaglandins; D015107:4-Butyrolactone; C013905:cyclopentenone