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Regiochemistry-Directed Syntheses of Polyhydroxylated Alkaloids from Chiral Aziridines

Title
Regiochemistry-Directed Syntheses of Polyhydroxylated Alkaloids from Chiral Aziridines
Author
조천규
Keywords
alkaloids; asymmetric synthesis; aziridines; polyhydroxylated compounds; regiochemistry
Issue Date
2015-12
Publisher
WILEY-V C H VERLAG GMBH
Citation
ASIAN JOURNAL OF ORGANIC CHEMISTRY, v. 4, NO 12, Page. 1399-1409
Abstract
In this study, two possible regiochemical pathways of aziridine ring opening, termed "regiochemistry-directed branches for 2-substituted aziridines" are described, providing easy access to two classes of compound from a common synthetic intermediate. Application of this synthetic strategy, with stereoselective dihydroxylation and reductive amination as the key steps, allowed the asymmetric synthesis of natural and unnatural polyhydroxylated alkaloids including the calyculin fragment C-33-C-37, 1,4-dideoxy-1,4-imino-l-ribitol and analogues of hyacinthacine, swainsonine, castanospermine, and deoxynojirimycin. The initial domino reactions consisted of aziridine ring opening and debenzylation, and reductive double annulations were established for the preparation of bicyclic pyrrolizidine and indolizidine-represented by 8-deoxyhyacinthacine and (3R)-methyl- 8-deoxyswainsonine-with remarkable stereoselectivity and in high yield.
URI
http://onlinelibrary.wiley.com/doi/10.1002/ajoc.201500285/abstract;jsessionid=343B8354E2D0E0F738CD0C873362706C.f03t01http://hdl.handle.net/20.500.11754/30052
ISSN
2193-5807; 2193-5815
DOI
10.1002/ajoc.201500285
Appears in Collections:
COLLEGE OF NATURAL SCIENCES[S](자연과학대학) > CHEMISTRY(화학과) > Articles
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