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Unsaturated 1,4‐ cis and 1,4‐ trans ‐Diaminotetradeoxycycloheptites—Enantiomerically Pure, Polyfunctionalized Tropa Derivatives by Enzymatic Hydrolysis
Author(s) -
FalkHeppner Manuela,
Keller Manfred,
Prinzbach Horst
Publication year - 1989
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198912531
Subject(s) - chemistry , yield (engineering) , hydrolysis , tropone , enzymatic hydrolysis , alcohol , organic chemistry , enzyme , stereochemistry , materials science , metallurgy
The compound anti‐cis ‐diepoxycycloheptene alcohol 1 (R H), prepared from tropilidene (tropone), is the starting material for an efficient synthesis of a variety of protected, enantiomerically pure 1, 4‐diaminotetradeoxycycloheptites appropriate for glycosidation reactions. Enzymatic hydrolysis of the tropa‐analogous meso ‐diacetate intermediates leads in 86–100% yield to monoacetates with ee values above 99%.