Total synthesis of lycoricidine via photochemical dearomative dihydroxylation

Lycoricidine;total synthesis;dearomative dihydroxylation

Holycross, Daniel Robert ; Sarlah ; David

关键词: Lycoricidine;    total synthesis;    dearomative dihydroxylation;   

Others  :  https://www.ideals.illinois.edu/bitstream/handle/2142/95520/HOLYCROSS-THESIS-2016.pdf?sequence=1&isAllowed=y

美国|英语

来源: The Illinois Digital Environment for Access to Learning and Scholarship

【 摘 要 】

Lycoricidine a member of the amaryllidaceae isocarbostyril alkaloid family of natural products isolated from bulbs of plants in the amaryllidaceae family, which include the common daffodil. The compound has been demonstrated to possess significant biological activity against a wide range of cancer cell lines. As such, lycoricidine, as well other members of the amaryllidaceae isocarbostyril alkaloid family, has been the target of a number of total syntheses by many investigators, which are outlined in detail herein.This thesis documents a novel total synthesis of lycoricidine utilizing a photochemical dearomative dihydroxylation of bromobenzene. Modified Narasaka-Sharpless dihydroxylation generates a product bearing both the electrophile and nucleophile for an unprecedented transpositive Suzuki coupling. Hetero-Diels-Alder cycloaddition is used to form the syn-1,4-amidoalcohol functionality. This new route completes the total synthesis of lycoricidine in eight steps, shorter than any previously completed synthesis.