103259-94-5Relevant articles and documents
Total Synthesis of the Pseudoguaianolide (+)-Confertin
Quinkert, Gerhard,Schmalz, Hans-Guenther,Walzer, Egon,Gross, Stefan,Kowalczyk-Przewloka, Teresa,et al.
, p. 283 - 316 (2007/10/02)
The first total synthesis of the pseudoguaianolide (+)-confertin (1) begins with the preparation of the enantiomerically pure cyclopropane derivative 6b and its stereospecific ring expansion furnishing the five-membered ring A-building block 8a.The AB ketone 21d is produced by intermolecular Michael addition, Lewis acid catalyzed intramolecular hetero-ene reaction, and a pair of oxidation/reduction reactions.Fusion of the heterocyclic five-membered ring and α-methylenation of the ABC intermediate 35c is accomplished by well-known technology.The structure of essential synthetic intermediates has been determined by 2D-NMR, CD spectroscopy, or single crystal X-ray analysis.The whole synthesis starts from α-chloroacetone and reaches the target compound 1 after 22 steps.