Total synthesis of the sesquiterpene (+/-)-illudin C via an intramolecular nitrile oxide cycloaddition.
[reaction: see text] A convergent total synthesis of illudin C is described. The tricyclic ring system of the natural product was quickly assembled from cyclopropane and cyclopentene precursors via a novel oxime dianion coupling reaction and a subsequent intramolecular nitrile oxide-olefin cycloaddition.
Aungst
R A
RA
Department of Chemistry, Pennsylvania State University, University Park, PA 16802, USA.
Chan
C
C
Funk
R L
RL
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D003500:Cyclization; D007202:Indicators and Reagents; D009570:Nitriles / Q000737:chemistry*; D010087:Oxides; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes; D013141:Spiro Compounds / Q000138:chemical synthesis*
D000900:Anti-Bacterial Agents; D007202:Indicators and Reagents; D009570:Nitriles; D010087:Oxides; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes; D013141:Spiro Compounds; C101779:illudin C