Enantioselective synthesis of (-)-roccellaric acid.
[reaction in text] A new strategy for the synthesis of anti-4,5-disubstituted gamma-butyrolactones starting from inexpensive furan-2-carboxylic methyl ester was developed. By applying this methodology, the enantioselective synthesis of (-)-roccellaric acid ((-)-17) was accomplished using a copper(I)-catalyzed asymmetric cyclopropanation, a tin(IV)-catalyzed retroaldol/lactonization sequence of cyclopropanols, and a ruthenium-catalyzed intermolecular metathesis reaction as key steps.
Böhm
C
C
Institut für Organische Chemie, Universität Regensburg, Universitätsstr. 31, 93053 Regensburg, Germany.
Reiser
O
O
D015107:4-Butyrolactone / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry*; D003300:Copper / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D012428:Ruthenium / Q000737:chemistry; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014001:Tin / Q000737:chemistry
D005663:Furans; C428504:roccellaric acid; D014001:Tin; D003300:Copper; D012428:Ruthenium; D015107:4-Butyrolactone