• Bulletin of the Korean Chemical Society
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• v.28 no.8
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• pp.1401-1404
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• 2007

An efficient Pictet-Spengler type reaction of N,O-acetal TMS ethers for the practical synthesis of 1-substituted tetrahydroquinolines, medicinally important alkaloids, has been accomplished. To demonstrate the versatility of this novel procedure, the total synthesis of calycotomine, a representative 1-hydroxymethyl substituted tetrahydroisoquinoline, is also described.

• YAKHAK HOEJI
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• v.53 no.3
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• pp.161-164
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• 2009

Synthetic studies directed toward an asymmetric total synthesis of calycotomine, an representative tetrahydroisoquinoline, are described. The application of N-tert-butane sulfinyl chiral auxiliary to the Pictet-Spengler type reaction for the efficient synthesis of tetrahydroisoquinoline skeleton has been also investigated.

• Journal of the Korean Applied Science and Technology
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• v.36 no.2
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• pp.676-684
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• 2019

The Pictet-Spengler reactions have widely known for the organic synthesis or biosynthesis of biologically active compounds, tetrahydro-${\beta}$-carbolines. We have developed the simple and efficient synthetic method for the synthesis of ${\beta}$-carbolines in water. Their chemical structures were characterized by nmr and UPLC/MS/QTOF. Calculated masses of compound 1 ($C_{17}H_{17}N_2$ 249.1392), 2 ($C_{17}H_{23}N_2$ 255.1861), 3 ($C_{19}H_{21}N_2O_3$ 325.1552) and 4 ($C_{19}H_{19}N_2O$ 279.1497) were almost identical with the detected masses of compound 1 (249.1315), 2 (255.1789), 3 (325.1460) and 4 (279.1364) respectively. Those synthesized four compounds showed strong antibiotic activity against the common E. coli.

• Bulletin of the Korean Chemical Society
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• v.12 no.4
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• pp.380-382
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• 1991

Pictet-Spengler reaction of the N-hydroxytryptophan ethyl ester (4) with N-protected thiazolidine aldehyde (8) has been carried out. The product, compound (9b), might be a possible precursor for the eudistomins C, E, K, and L.

• Journal of the Korean Applied Science and Technology
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• v.29 no.2
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• pp.248-256
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• 2012

Aza-indoles are important pharmacophores that have similar size and biological properties of indole. Here we have synthesized 4- and 7-azaindole tryptamines and showed that they are successfully incorporated in the biosynthesis of monoterepene indole alkaloids (MIAs) to form novel azaindole alkaloids by enzymatic reactions of strictosidine synthase(STR) and strictosidine glucosidase(SDG) monitored by UPLC/MS. By using HPLC equipped with a HPLC photo diode array(PDA) detector, each of the UV spectra of azaindole alkaloids was obtained and characterized. When hydrophilicity of azaindole alkaloids was compared, 4-azaindole alkaloids were more hydrophilic than 7-azaindole alkaloids.