ISSN:
0947-6539
Keywords:
aminopolyols
;
asymmetric aminations
;
asymmetric epoxidation
;
asymmetric hydroxylation
;
didemnins
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
A novel strategy for the synthesis of isostatine derivatives has been developed. Contrary to previous approaches to isostatine, a non-proteinogenic amino acid that is an essential component of the didemnins, the present synthesis does not require the intermediacy of the expensive amino acid D-allo-isoleucine, the starting material being commercially available enantiopure (S)-2-methyl-1-butanol. Steps in the sequence include catalytic asymmetric epoxidation, regioselective titanium-promoted opening of an epoxy alcohol with an ammonia equivalent, stereospecific generation of an N-Bocamino epoxide and its nucleophilic opening by a cyanide anion. Application of this method has permitted the enantioselective preparation of isostatine methyl ester and, for the first time, of isostatine amide, both in fully protected form.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/chem.1460020814
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