One-pot, four-different-component annulations: flexible and efficient conversion of n-sized cycloalkenones into n+4 alkenolides
1987; Elsevier BV; Volume: 28; Issue: 43 Linguagem: Inglês
10.1016/s0040-4039(00)95592-8
ISSN1873-3581
AutoresGary H. Posner, E. ASIRVATHAM, Kevin S. Webb, Sang‐sup Jew,
Tópico(s)Coordination Chemistry and Organometallics
ResumoFive-, six-, and seven-membered conjugated cycloalkenones undergo one-pot conjugate addition with tri-n-butyltinlithium followed by 1,4-addition to vinyl ketones and then aldol addition to aldehydes leading to cyclic hemiketals 2. Lead tetraacetate oxidative fragmentation produces various 4-atom enlarged, vicinally disubstituted, regiospecifically and stereospecifically unsaturated macrolides 3.
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