Unsaturated 1,4‐ cis  and 1,4‐ trans ‐Diaminotetradeoxycycloheptites—Enantiomerically Pure, Polyfunctionalized Tropa Derivatives by Enzymatic Hydrolysis | Zendy

FalkHeppner Manuela | Zendy; Keller Manfred | Zendy; Prinzbach Horst | Zendy

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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%.

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