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2.1.5.3.1 Synthesis of Strictosidine Analogues with Substituents on the Indole Unit

DOI: 10.1055/sos-SD-215-00081

Ilari, A.; Bonamore, A.; Boffi, A.Science of Synthesis: Biocatalysis in Organic Synthesis, (20152168.

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.

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References