The asymmetric synthesis of the cyclohexyl fragment of FK-506 is reported. This new synthesis (five steps, 30% overall yield) starts, for the first time, from (S)-(-)-3-cyclohexenecarboxylic acid (S-2) instead of the commonly used R form (acid R-2) and utilizes an epimerization reaction. The overall yield is improved to 35% by recycling recovered starting product (hydroxy ester 7c) from the epimerization step.
PRACTICAL, ASYMMETRIC-SYNTHESIS OF THE CYCLOHEXYL C-28-C-34 FRAGMENT OF THE IMMUNOSUPPRESSANT FK-506 VIA (S)-(-)-3-CYCLOHEXENECARBOXYLIC ACID
CROTTI, PAOLO;PINESCHI, MAURO;
1992-01-01
Abstract
The asymmetric synthesis of the cyclohexyl fragment of FK-506 is reported. This new synthesis (five steps, 30% overall yield) starts, for the first time, from (S)-(-)-3-cyclohexenecarboxylic acid (S-2) instead of the commonly used R form (acid R-2) and utilizes an epimerization reaction. The overall yield is improved to 35% by recycling recovered starting product (hydroxy ester 7c) from the epimerization step.File in questo prodotto:
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