期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 78, 期 10, 页码 4779-4800出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo400324t
关键词
-
资金
- National Institutes of Health (NIH) [GM63723]
- Oregon State University
The formal syntheses of C-5-epi-senepodine G and C-5-epi-cermizine C have been accomplished through a novel diastereoselective, intramolecular amide Michael addition process. The total synthesis of cermizine D has been achieved through use of an organocatalyzed, heteroatom Michael addition to access a common intermediate. Additional key steps of this sequence include a matched, diastereoselective alkylation with an iodomethylphenyl sulfide and sulfone-aldehyde coupling/reductive desulfurization sequence to combine the major subunits. The utility of a Hartwig-style C-N coupling has been explored on functionally dense coupling partners. Diastereoselective conjugate additions to alpha,beta-unsaturated sulfones have been investigated, which provided the key sulfone intermediate in just six steps from commercially available starting materials. The formal syntheses of senepodine G and cermizine C have been accomplished through an intramolecular cyclization process of a N-Boc-protected piperidine sulfone.
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