Concise Synthesis and Antimicrobial Evaluation of the Guanidinium Alkaloid Batzelladine D: Development of a Stereodivergent Strategy.

ABSTRACT: Herein, we describe a stereodivergent route to (±)-batzelladine D (2), (+)-batzelladine D (2), (-)-batzelladine D (2), and a series of stereochemical analogues and explore their antimicrobial activity for the first time. The concise synthetic approach enables access to the natural products in a sequence of 8-12 steps from readily available building blocks. Highlights of the synthetic strategy include gram-scale preparation of a late stage intermediate, pinpoint stereocontrol around the tricyclic skeleton, and a modular strategy that enables analogue generation. A key bicyclic β-lactam intermediate not only serves as the key controlling element for pyrrolidine stereochemistry but also serves as a preactivated coupling partner to install the ester side chain. The stereoc

SUBMITTER: Lin YC 

PROVIDER: S-EPMC7685371 | biostudies-literature | 2020 May

REPOSITORIES: biostudies-literature