Regioselective synthesis of trisubstituted 2,3-dihydrofurans from donor-acceptor cyclopropanes or from reaction of the Corey ylide with alpha-sulfenyl-, alpha-sulfinyl-, or alpha-sulfonylenones.
[reactions: see text] Regioselective synthesis of 2,4,5- or 3,4,5-trisubstituted 2,3-dihydrofurans has been realized by using donor-acceptor cyclopropanes or by a Corey ylide reaction with alpha-sulfenyl-, alpha-sulfinyl-, or alpha-sulfonylenones. The method allowed a straightforward synthesis of the natural product calyxolane B.
Bernard
Angela M
AM
Dipartimento di Scienze Chimiche, Università degli studi di Cagliari, Cittadella Universitaria di Monserrato, S.S 554, Bivio per Sestu, I-09042 Monserrato (Cagliari), Italy.
Frongia
Angelo
A
Piras
Pier P
PP
Secci
Francesco
F
Spiga
Marco
M
D003521:Cyclopropanes / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013457:Sulfur Compounds / Q000737:chemistry*
D003521:Cyclopropanes; D005663:Furans; D013457:Sulfur Compounds; C073812:2,3-dihydrofuran