Total Synthesis of Naturally Occurring Amaryllidaceae Alkaloid, (+)-11-Hydroxyvittatine

Roy, Tiyasa (2025) Total Synthesis of Naturally Occurring Amaryllidaceae Alkaloid, (+)-11-Hydroxyvittatine. Masters thesis, Indian Institute of Science Education and Research Kolkata.

Text (MS Dissertation of Tiyasa Roy (23MP008)) 23MP008_Thesis_file.pdf - Submitted Version Restricted to Repository staff only Download (3MB)

Abstract

The first catalytic asymmetric total synthesis of naturally occurring (+)-11-hydroxyvittatine (1a) has been achieved in 9 steps and an overall yield of 14.6% from commercially available materials. The strategy includes developing an efficient and enantioselective synthetic route to access complex Amaryllidaceae alkaloids, focusing on the total synthesis of (+)-11- hydroxyvittatine (1a). These natural products, derived from the Amaryllidaceae plant family, are notable for their structural complexity and broad range of biological activities, including antiviral, antitumor, and anti-inflammatory properties. Key steps include a highly enantioselective CBS reduction (up to 92% ee), a strategic Mitsunobu reaction, and a microwave-assisted carbonyl-ene cyclization that establishes three stereocenters in one step. This is followed by a diastereoselective allylic oxidation and a Pictet–Spengler reaction to complete the core structure. The methodology developed here lays a foundation for synthesizing other complex Amaryllidaceae alkaloids, including derivatives like hamayne (1b, 1f–h), which remain under active investigation

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