Chiral synthesis of 3,4-disubstituted 2-azetidinones from (R,R)-(+)-tartaric acid
✍ Scribed by Alice Gateau-Olesker; Jeannine Cléophax; Stephan D. Géro
- Publisher
- Elsevier Science
- Year
- 1986
- Tongue
- French
- Weight
- 214 KB
- Volume
- 27
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
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## 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
Summahy: E-(RI -5-tfydkoxy-Z-hexenoic acid (4) and the acetovúde 06 E-(4R, 5R, 7R) -tihydtoxy-2--ootenoic acid (31 am joined tu &e, a&tm depkotecLLon, (+J-coUeeeRo&oL (ll. The. nqnthue,s 06 thc two hq&oxq-ati& @am poey-(RI -3-hydhoxy-bt&anoa& (P/+BJ uñd (-)-Ramtah¿c acid, ~enpec.a%wLq, am otimd.
Taking advantage of the high functionality of an enantiopure protected syn-2R-amino-l,3,4-triol derivative, easily available on a multigram scale from Disoascorbic acid, several biologically active compounds have been synthesized such as the (2S,3R)-3-amino-2-hydroxydecanoic acid (AHDA), the N-termi