Total synthesis of optically active chanoclavine-I
โ Scribed by Yuusaku Yokoyama; Kazuhiro Kondo; Masako Mitsuhashi; Yasuoki Murakami
- Book ID
- 104258730
- Publisher
- Elsevier Science
- Year
- 1996
- Tongue
- French
- Weight
- 221 KB
- Volume
- 37
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
The total synthesis of optically active clianochvine-I, an ergot alkaloid, was accomplished using palladium-catalyzed intramoleeular cyclization (Heck reaction) as a key step. The conjugate ester (6) was obtained in 2 steps from optically active 4-bmmotryptophan (10), and the cyclization of 6 proceeded smoothly without racemization to give the key intermediate, trieyelie tetrahydrobenz [c,d]indole derivative (7), in high yield.
๐ SIMILAR VOLUMES
We then focused our attention on the asymmetric formation of the CT-Cl0 bond of the nitro acetate 3 using paRadium xero complexes 23 . The best results of this key cyclisation were obtained by using Pd(dba)g and (S,S)-CHIRAPHOS as the chiral diphosphine, in THF at teflux I8 . We optimised these resu