Indole Alkaloids Syntheses

• Main Authors: Basuki Gunawan, 陳群貴
• Other Authors: Ho Tse-Lok
• Format: Others
• Language: en_US
• Published: 2005
• Online Access: http://ndltd.ncl.edu.tw/handle/13493614361896604690

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.