Tetrahedron p. 539 - 544 (1992)
Update date:2022-08-03
Topics:
Chini
Crotti
Macchia
Pineschi
Flippin
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.
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