Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 3, Pages 1340-1351Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b01861
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Funding
- Natural Sciences and Engineering Research Council of Canada (NSERC) [04079]
- Fonds de recherche nature et technologie Quebec for the Centre in Green Chemistry and Catalysis [FRQNT-2020-RS4-265155-CCVC]
- Universite de Montreal
- Shastri Indo-Canadian Institute, India
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Sets of azabicyclo[X.Y.0]alkanone amino acids have been effectively used to identify active conformers in peptide-based drug discovery, but they usually require multiple routes to synthesize. Employing a common method from the same nine-membered unsaturated lactam precursor, we developed conditions for stereo- and regiochemical transannular cyclizations to synthesize three different indolizidin-2- and 9-one amino acid (I(2)aa and I(9)aa) analogues. For example, (3S,5R,6R,9S)- and (3S,SS,6S,9S)-I(2)aa diastereomers were prepared from hexahydro-1H-azonines by using iodine in THE and in MeCN with DIB as an additive. The regioselectivity of the transannular cyclization was influenced by amine protection to favor the synthesis of the I(9)aa isomer. Moreover, side chains were added onto the I(2)aa and I(9)aa ring systems by way of olefin intermediates that underwent Pd-catalyzed C-H bond activation and allylic oxidation.
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