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Please login to access the full content or check if you have access via2.1.5.3.1 Synthesis of Strictosidine Analogues with Substituents on the Indole Unit
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Ilari, A.; Bonamore, A.; Boffi, A., Science of Synthesis: Biocatalysis in Organic Synthesis, (2015) 2, 168.
Catalytic methodologies have been developed to generate chiral tetrahydro-β-carbolines 13 from substituted tryptamines 12 and secologanin (4). The transformation of substituted tryptamines is achieved using wild-type RsSTS or the engineered RsSTSVal208Ala mutant and CrSTSVal214Met or CrSTSPhe232Leu mutants, as shown in Scheme 7. Tryptamines with substituents in the 4–7 positions of the six-membered A-ring have been synthesized separately or are commercially available, as described in the relevant references.[28,29] Secologanin is obtained from Lonicera tatarica using the procedure reported by Bernhardt and co-workers.[29] Selected examples of synthetic procedures are presented below.
Meeeee 8 Meeeeeeee ee Meeeeeeeeeeee Meeeeeeee eeee Meeeeeeeeeee ee eee Meeeee Meee[88,88]
| M8 | M8 | M8 | M8 | M8 | Meeeeeeeeeeee Meeeeeeee | Mee |
|---|---|---|---|---|---|---|
| M | M | M | M | M | MeMMMMee888Mee, MeMMMMee888Mee, MeMMMee | [88] |
| M | M | Me | M | M | MeMMMMee888Mee | [88] |
| MM8MM | M | M | M | M | MeMMMMee888Mee | [88] |
| M | M | Me | M | M | MeMMMMee888Mee | [88] |
| M | M | Me | M | M | MeMMMMee888Mee | [88] |
| M | M | M | M | M | MeMMMee | [88] |
| M | Me | M | M | M | MeMMMee | [88] |
| M | MMe | M | M | M | MeMMMee | [88] |
| M | M | M | M | M | MeMMMee | [88] |
| M | M | MM | M | M | MeMMMee | [88] |
| M | M | M | M | M | MeMMMee | [88] |
| M | M | M | MMe | M | MeMMMee | [88] |
| M | M | M | M | M | MeMMMee | [88] |
| M | M | M | M | Me | MeMMMee | [88] |
| M | M | M | M | MMe | MeMMMee | [88] |
| M | M | Me | M | M | MeMMMMee888Mee | [88] |
| M | M | MMe | M | M | MeMMMMee888Mee | [88] |
| M | M | M | M | M | MeMMMMee888Mee, MeMMMee | [88] |
| M | M | MM | M | M | MeMMMMee888Mee, MeMMMee | [88] |
| M | M | M | Me | M | MMMMeMee888Mee, MeMMMee | [88] |
| M | M | M | MMe | M | MeMMMMee888Mee, MeMMMee | [88] |
| M | M | M | M | M | MeMMMMee888Mee, MeMMMee | [88] |
e “ee” eeeeee eeeeeee eeee-eeee eeeeee.
Meeeeeeeeeee Meeeeeeee
88-Meeeeeeeeeeeeeeeeee (88, M8 = M8 = M8 = M8 = M; M8 = Me); Meeeeee Meeeeeeee:[88]
8-Meeeeeeeeeeeeeee eeeeeeeeeeeee (8.88 ee; 8.8 µeee) eee eeeeeeeeeee (8; 8.888 ee; 8.8 µeee) eeee eeeeeeeee ee eee eeeeeeee ee eeee Mee-eeeeee MeMMMMee888Mee eeeeee (888 µe) ee 88 eM eeeeeeeee eeeeeeeee eeeeee (eM 8.8; 8.8 eM). Mee eeeeeeee eee eeeeeeeee ee 88 °M eee 88 eee. Mee eeeeeee eee eeee eeeeeee eeee MeMM (8 eM), eeeeeeeeeee, eee eee eeeeeeeeeee eee eeeeee-eeeee. M8M (8 eM) eee 8.8 M Me8MM8 (8.8 eM) eeee eeeee ee eee eeeeeee. Mee eeeeeee eee eeeeeeeee eeee M8 eee eee eeeeee eee 8 e ee 88 °M. MeMe eee eeeee eee eeeeeeeeee eee eee eeeeeee eee eeeeeeeee eeee MeMMe (8 × 8 eM). Mee eeeeeeee eeee eeeeeeee eee eeeeeeeeeeee eee eee eeeeeee eee eeeee.
(8M)-8-(Meeeeeeeeeeee)eeeeeeeeeeeee (88, M8 = MM8MM; M8 = M8 = M8 = M8 = M); Meeeeee Meeeeeeee:[88]
M eeee ee (M)-8-eeeee-8-(8M-eeeee-8-ee)eeeeee-8-ee (888 ee, 8 eeee, 8 eeeee) ee MeMM (88 eM; 8% e/e eeeee eeeeeeeeeeeee ee eeeeeee eeeeeee) eee eeeeeeee eeeeeeeeeee (8; 888 ee, 8 eeee, 8 eeeee) eeee eeeee ee eeeeeee 88 eM ee eeeeee eeeeeeeee eeeeee (eM 8.8; 888 eM). Meee-eeeeeee eeeeeeeeee MeMMMMee888Mee[88] eee eeee eeeee (88 eM, 8% e/e) eee eee eeeeeeee eee eeeeeeeee ee 88 °M eee 88 e. Meee ee eee M8M eee eeeeeee eeeee e eeeeee eeeeeeeeee eee MeMM (eee eeeeeee) eee eeeee ee eeeeeeeeeee eee eeeeeee. Meeeeeeeee eee eeeeeeeeeee ee eee eeeeeeeee eeeeeee eeeeeeee e eeeeee eee. Mee eee eee eeeeeeeee ee MeMM (88 eM) eee eeeeeeee ee eeeeeeeeeee MMMM (eeeeeeee-eeeee eeeeee, 8-eM eeeeeeeeee, eeeeeeee 88:88 ee 88:88 M8M eeeeeeeeee 8.8% MMM/MeMM eeee 88 eee). Meeeeeeeeeee eeee (8M)-8-(eeeeeeeeeeeee)eeeeeeeeeeeee eee eeeeeeee ee e eeee eeeeee eeeeeeeee eeeee; eeeee: 888 ee (88%); ee >88.8%.
88-Meeeeeeeeeeeeeeeeee (88, M8 = M8 = M8 = M8 = M; M8 = Me); Meeeeee Meeeeeeee:[88]
8-Meeeeeeeeeeeeeee eeeeeeeeeeeee eeee (888 ee, 8 eeee, 8 eeeee) eee eeeeeeeeeee (8; 888 ee, 8 eeee, 8 eeeee) eeee eeeeeeeee ee eeeeeee 88 eM eeeeeee eeeeee eeeeeeeee eeeeee (eM 8.8; 888 eM). MeMMMMee888Mee eeeee eeeeeee[88] eee eeee eeeee (88 eM, 8% e/e) eee eee eeeeeeee eee eeeeeeeee eee 88 e ee 88 °M. M8M eee eeeeeee eeeee e eeeeee eeeeeeeeee eee MeMM (eee eeeeeee) eee eeeee ee eeeeeeeeeee eee eeeeeee. Meeee eeeeeeeeee eee eeeeeeeeee, eee eeeeeee eee eeeeeeeeee ee eeeeee e eeeeee eeeee. Mee eeeee eee eeeeeeeee ee MeMM (88 eM) eee 88 ee ee eee eeeeeee eee eeeeeeee ee eeeeeeeeeee MMMM (eeeeeeee-eeeee eeeeee, 8-eM eeeeeeeeee, eeeeeeee 88:88 ee 88:88 M8M eeeeeeeeee 8.8% MMM/MeMM eeee 88 eee). Meeeeeeeeeee eeee 88-eeeeeeeeeeeeeeeeeee eee eeeeeeeeeeeee ee MMM; ee >88.8%.
References
| [28] | Meeee, M. M.; Meeeeeee, M.; Meeeeee, M.; Meeeeeee, M.; Meeee, M.; Meeüeee, M.; Meöeeeee, M., Meee. Meee. (Meeeee, M. M.), (8888) 88, 888. |
| [29] | Meeeeeeee, M.; MeMee, M.; MʼMeeeee, M. M., Meee. Meee. (Meeeee, M. M.), (8888) 88, 888. |
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