Secorubenine, a Monoterpenoid Indole Alkaloid Glycoside from <i>Adina rubescens</i>: Isolation, Structure Elucidation, and Enantioselective Total Synthesis

Abstract

A new pentacyclic monoterpenoid indole alkaloid glycoside named secorubenine (1) was isolated from the heartwood of Adina rubescens, collected in Indonesia. The structure was elucidated by spectroscopic analysis and chemical modification of isolated secorubenine (1). The bioinspired enantioselective total synthesis of 1 was accomplished in 12 steps, whereafter its structure was determined and the absolute stereochemistry was confirmed.

Bioinspired Total Syntheses of Secologanin-Related Natural Products: A Demonstration of the Power of Secologanin in the Flask

“…As a result, 31 was isolated from the bark of Adina rubescence , which originally contained 4 , and we named this molecule ‘secorubenine’. 8c…”

Bioinspired Total Synthesis of (+)-Kopsiyunnanine B

“…We have recently achieved a collective total synthesis of monoterpenoid indole alkaloids along a biosynthetic tree diagram. [13][14][15][16][17][18][19][20][21] In this study, we conceived an alternative biosynthetic hypothesis for 1 (Chart 2). Our proposed biosynthesis begins with a connection by the reductive amination of tryptamine and secologanin (2).…”