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Application of the gold(I)-Catalyzed aldol reaction to a stereoselective synthesis of (2S, 3R, 4R, 6E)-3-Hydroxy-4-methyl-2-(methylamino)oct-6-enoic Acid ( = MeBmt), Cyclosporin's unusual amino acid

✍ Scribed by Antonio Togni; Stephen D. Pastor; Grety Rihs

Publisher
John Wiley and Sons
Year
1989
Tongue
German
Weight
507 KB
Volume
72
Category
Article
ISSN
0018-019X

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✦ Synopsis

Introduction. ~ Stereoselective C-C bond forming reactions catalyzed by chiral transition-metal complexes are a topic of fundamental importance [l]. In 1986, Hayashi and Zto reported an elegant asymmetric synthesis of dihydrooxazoles by an efficient gold(1)-catalyzed coupling of aldehydes with 2-isocyanoacetates in the presence of chiral ferrocenylphosphines of type 1 and the gold(1) complex 2 as a catalyst precursor [2]. The high diastereo-and enantioselectivity obtained in this type of aldol reaction constitutes a powerful approach to optically active j3-hydroxy-a -amino acids.

Hayashi and It0 reported subsequently the design of more sophisticated ferrocenylphosphine ligands 131 but investigated only to a limited extent the influence of Fe

📜 SIMILAR VOLUMES

Synthesis of Cyclosporine. I. Synthesis
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
✍ Roland M. Wenger 📂 Article 📅 1983 🏛 John Wiley and Sons 🌐 German ⚖ 948 KB

## 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