Synthesis of monatin-A high intensity natural sweetener

Details Synthesis of monatin-A high intensity natural sweetener Synthesis of monatin-A high intensity natural sweetener

1998-08-06

1999-11-30

McKane, Joseph K.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D20918

Patent

active

059945591

ABSTRACT:
The high intensity natural sweetener monatin, an .alpha.-amino acid (1) is synthesized from readily available starting materials. Regiospecific ring opening of epoxide (9) with indole magnesium bromide yields lactone (11). Amination of (11) followed by saponification yields Monatin.

REFERENCES:
patent: 4975298 (1990-12-01), Van Wyk et al.
patent: 5128164 (1992-07-01), Van Wyk et al.
patent: 5128482 (1992-07-01), Olivier et al.
Holzapfel, et al., A simple cycloaddition approach to a racemate of the natural sweetener monatin, Synthetic Communications, 24(22), 3197-3211 (1994).
Vleggaar, et al., Structure elucidation of monatin, a high-intensity sweetner isolated from the plant Schlerochiton ilicifolius, J. Chem. Soc. Perkin Trans., 3095-3098, (1992).

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