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Synthesis of Cyclosporine. I. Synthesis of enantiomerically pure (2S,3R,4R,6E)-3-hydroxy -4-methyl-2-methylamino-6-octenoic acid starting from tartaric acid

✍ Scribed by Roland M. Wenger

Publisher
John Wiley and Sons
Year
1983
Tongue
German
Weight
948 KB
Volume
66
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Starting from R,R‐(+)‐tartaric acid, the synthesis of (2__S__,3__R__,4__R__6__E__)‐3‐hydroxy ‐4‐methyl‐2‐methylamino‐6‐octenoic acid in 24 steps is reported. This novel amino acid is found in the cyclic undecapeptide cyclosporin A, isolated from the fungal strain Tolypocladium inflatum GAMS. Its stereospecific synthesis allowed, for the first time, the isolation and characterization of the new amino acid previously reported as the ‘C‐9‐amino acid’ [1].

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