119th General Meeting of the KCS

Type Symposium
Area Current Trends in Organic Chemistry Ⅲ: Synthetic Methodology and Catalysis
Room No. 302호
Time FRI 14:30-:
Code ORGN3-1
Subject Tandem [3,3]-sigmatropic rearrangement/cyclization of diaryl hydrazide for the efficient total syntheses of ningalins D and G
Authors 김장엽, 조천규*
한양대학교 화학과, Korea
Abstract

Ningalin D is a purple colored benzocarbazole marine alkaloid first isolated by Kang et al. from a western Australian unidentified ascidian belonging to the genus Didemnum. More recently, Capon et al. isolated a closely related marine natural product, named as ningalin G, from the extract of a Southern Australian marine ascidian, Didemnum, and characterized its structure as shown below (Figure 1). As a part of our ongoing investigation on the synthetic utility of aryl hydrazides, we have elaborated a new synthetic route to both ningalin D (1a) and G (2), by way of 7H-dibenzo[c,g]carbazole as the key juncture. Subsequent installation of 3,4-dimethoxyphenyl groups followed by a series of oxidation reactions permitted the total syntheses of the titled marine alkaloids in good overall yields.

E-mail ccho@hanyang.ac.kr