A convergent synthetic approach to a chiral, nonracemic CDEF analog of nogalamycin

An approach to the synthesis of the CDEF rings of nogalamycin is described. The synthesis involves two key cycloadditions: (1) The regioselective addition of (2S)-2,3-O-cyclohexylideneglyceronitrile oxide with furan to yield the furoisoxazoline 7 and (2) the regioselective Bradsher cycloaddition of...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 57; no. 2; pp. 644 - 651
Main Authors Yin, Htwe, Franck, Richard W, Chen, Shun Le, Quigley, Gary J, Todaro, Louis
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.01.1992
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Condensed benzenic and aromatic compounds
Exact sciences and technology
Organic chemistry
Physical Sciences
Preparations and properties
Science & Technology
OXIDATION
ALCOHOLS
ORGANIC-SYNTHESIS
STRUCTURAL ELUCIDATION
NITRILE OXIDE
RING SYSTEM
AMINO-SUGARS
CONGENERS
CYCLO-ADDITIONS
DERIVATIVES
Cycloaddition
Regioselectivity
Aminoglycoside
Quinone
Nitrile oxide
Condensed benzenic compound
Organic sulfide
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Summary:An approach to the synthesis of the CDEF rings of nogalamycin is described. The synthesis involves two key cycloadditions: (1) The regioselective addition of (2S)-2,3-O-cyclohexylideneglyceronitrile oxide with furan to yield the furoisoxazoline 7 and (2) the regioselective Bradsher cycloaddition of 7 with isoquinoline salt 8, induced by a pressure of 6 kbar, to attach the amino sugar moiety to the aromatic ring.
Bibliography:ark:/67375/TPS-L3QKZN16-W
istex:8689A6EC6393DD217B24C32365082D8CCDB1B726
ISSN:0022-3263
1520-6904
DOI:10.1021/jo00028a045