| Summary: | 博士 === 國立交通大學 === 應用化學系所 === 94 === Synthetic studies towards several indole alkaloids were pursued, utilizing molecular symmetry to guide the synthetic design. All tetrahydro-β-carbolines intermediates described in this dissertation were constructed by reacting tryptamine with symmetrical aldehydes via acid-induced Pictet-Spengler reaction:
- Total synthesis of tangutorine 1 started from the reaction of tryptamine with aldehyde 3 - derived from symmetrical 1,3-cyclohexadione - to build the key intermediate 2 that has the correct stereochemistry of tangutorine 1.
- Total synthesis of Eburnamonine 7 was conducted via a spirocyclic intermediate 12, formed by reacting tryptamine with symmetrical 5-membered ring aldehyde 11c.
- Formal synthesis of vallesamidine 20 was conducted via intermediate 25, formed by reacting tryptamine with symmetrical 7-membered ring aldehyde 24.
- Synthetic study on aspidospermidine 39 was conducted via a spirocyclic intermediate 47, formed by reacting tryptamine with symmetrical tetrahydropyranyl aldehyde 49c.
- Synthetic study on oxogambirtannine 40 was conducted by reacting tryptamine with symmetrical 2-aryl substituted acetaldehyde 51.
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