Synthesis of furano[2,3-c]pyran-3-one and thieno[2,3-c]pyran-3-one derivatives through the coupling of 3-alkynyl-2-heteroaromatic carboxaldehydes with Fischer carbene complexes: total synthesis of a Baccharis-derived cadinene derivative.
The coupling of Fischer carbene complexes with 3-alkynyl-2-heteroaromatic carboxaldehyde derivatives has been examined. The reaction affords pyrones fused to furans or thiophenes in a single step. The compounds are stable enough for isolation. If the carbene complex features a remote alkene substituent, a subsequent Diels-Alder reaction can occur. This reaction has been used as the key step in the synthesis of a naturally occurring cadinene derivative.
Zhang
Yanshi
Y
Department of Chemistry & Biochemistry, New Mexico State University, MSC 3C, Las Cruces, New Mexico 88003, USA.
Herndon
James W
JW
D000447:Aldehydes / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry; D019659:Asteraceae / Q000737:chemistry*; D001685:Biological Factors / Q000138:chemical synthesis; D002384:Catalysis; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis*; D006838:Hydrocarbons; D006868:Hydrolysis; D007659:Ketones / Q000737:chemistry; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D011753:Pyrones / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013816:Thermodynamics; D013876:Thiophenes / Q000138:chemical synthesis*
D000447:Aldehydes; D000475:Alkenes; D000480:Alkynes; D001685:Biological Factors; D005663:Furans; D006838:Hydrocarbons; D007659:Ketones; D011753:Pyrones; D013876:Thiophenes; C030011:carbene; D008697:Methane