A general procedure for the synthesis of stereochemically pure conduritol derivatives practical also for solid-phase chemistry.
A straightforward synthetic protocol apt to synthesize a library constituted by all conduritol stereoisomers in solution phase is described and successfully applied to some polymer-supported substrates. During the solid-phase sequence, an unprecedented rearrangement of a resin-bound sulfone performed under the Ramberg-Bäcklund conditions appears of particular interest. Upon treatment with Me(3)Si-I, thiepanes supported on resin are found to undergo regio- and stereospecific ring contraction to a six-membered ring system with traceless cleavage from the solid support.
Cerè
Vanda
V
Dipartimento di Chimica Organica "A. Mangini", University of Bologna, Viale Risorgimento 4, I-40136 Bologna, Italy. cere@ ms.fci.unibo.it
Minzoni
Mirko
M
Pollicino
Salvatore
S
Ricci
Alfredo
A
Gasparrini
Francesco
F
Ciogli
Alessia
A
D'Acquarica
Ilaria
I
D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D003511:Cyclohexanols / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism; D013846:Thiepins / Q000737:chemistry*
D003511:Cyclohexanols; D013846:Thiepins