Journal
ORGANIC LETTERS
Volume 11, Issue 7, Pages 1531-1533Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol900142r
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Funding
- MICINN [CTQ2008-06557]
- Consolider Ingenio 2010 [CSID2007-00006]
- Xunta de Galicia [2007/XA084, INCITE08PXIB209024PR]
- MEC (Spain)
- Fundayacucho (Venezuela)
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TFA-promoted exo carbocyclizations of nonterminal 7-alkynals gave good to excellent yields of seven-membered cycloalkenones, a medium-sized functionalized ring present in natural products with relevant pharmacological properties. Nonterminal 5- and 6-alkynals also gave very good yields of the corresponding exo cyclopentenones and cyclohexenones. On the other hand, terminal 5-alkynals gave endo carbocyclizations to cyclohexenones. These carbocyclizations can be considered as tandem alkyne hydration/aldol condensation processes.
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