Synthetic studies of indotizidine and stemona alkaloids

การศึกษาการสังเคราะห์อัลคาลอยด์ในกลุ่มอินโดลิซิดีนและสเตโมนา

Name: Pijitra Bunrod

Name: พิจิตรา บุญรอด

LCSH: Alkaloids -- Synthesis -- Research

Abstract: Indolizidine is a major group of alkaloids, many of which possess interesting biological activities. Herein we report our synthetic studies toward two selected indolizidine alkaloids; Crispine A is a benzoindolizidine alkaloid which was isolated from the Chinese plant Carduus crispus. It has been used as folk medicine for treatment of stomachache and rheumatism and was recently also found that it inhibits the growth of cancer. We used Nacyliminium ion cyclization to construct the tricyclic dibenzylamino benzoindolizidine core of crispine A. Treatment of this reaction’s product with excess iodomethane in expecting Hoffmann elimination resulted in unexpected deamination. This serendipitously gave a known intermediate in a previously reported synthesis of crispine A.; Lentiginosine is a dihydroxylated indolizidine alkaloid. It was isolated from leaves of Astragalus lentiginosus. Biological activity studies have found that it is a glucosadase inhibitor and an anti-HIV agent. We used N-acyliminium ion cyclization and subsequent Cope elimination to synthesized a bicyclic diene indolizidinone intermediate for lentiginosine synthesis, albeit low yield was obtained in the last step. In addition, we plan to use N-acyliminium ion cyclization in tandem with lactonization in synthesis of another biologically active alkaloid, stemoamide’s tricyclic fused pyrorodinone-azepine-J-lactonestructure (tricyclic 5-7-5 system). In this thesis we report the progress of a model study aiming to create a tricyclic 5-6-6 system using the same reaction sequence as proof of concept.

มหาวิทยาลัยศิลปากร. สำนักหอสมุดกลาง

Address: นครปฐม (Nakorn Prathom)

Email: wangthapralibrary@gmail.com

Name: Punlop Kuntiyong

Role: Advisor

Name: พัลลภ คันธิยงค์

Role: อาจารย์ที่ปรึกษาหลัก

Created: 2013

Modified: 2025-06-06

Issued: 2025-06-06

วิทยานิพนธ์/Thesis

application/pdf

eng

DegreeName: Master of Science

Level: Master's Degree

Descipline: Organic Chemistry

Grantor: Silpakorn University

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