Total synthesis of landomycins Q and R and related core structures for exploration of the cytotoxicity and antibacterial properties

Yao-Hsuan Lai; Soumik Mondal; Hsin-Tzu Su; Sheng-Cih Huang; Mine-Hsine Wu; I.-Wen Huang; Tsai-Ling Yang Lauderdale; Jen-Shin Song; Kak-Shan Shia; Kwok-Kong Tony Mong

doi:10.1039/D1RA01088C

Total synthesis of landomycins Q and R and related core structures for exploration of the cytotoxicity and antibacterial properties†

Yao-Hsuan Lai,‡^a Soumik Mondal,‡^ab Hsin-Tzu Su,^ab Sheng-Cih Huang,^ab Mine-Hsine Wu,^c I.-Wen Huang,^c Tsai-Ling Yang Lauderdale,^c Jen-Shin Song,^c Kak-Shan Shia^c and Kwok-Kong Tony Mong

*^ab

Author affiliations

* Corresponding authors

^a National Chiao Tung University, Hsinchu 30010, Taiwan, Republic of China

^b National Yang Ming Chiao Tung University, Hsinchu 30010, Taiwan, Republic of China
E-mail: tmong@nycu.edu.tw

^c National Health Research Institutes, Miaoli County 35053, Taiwan, Republic of China

Abstract

Herein, we report the total synthesis of landomycins Q and R as well as the aglycone core, namely anhydrolandomycinone and a related core analogue. The synthesis features an acetate-assisted arylation method for construction of the hindered B-ring in the core component and a one-pot aromatization–deiodination–denbenzylation procedure to streamline the global functional and protecting group manuipulation. Subsequent cytotoxicity and antibacterial studies revealed that the landomycin R is a potential antibacterial agent against methicillin-resistant Staphylococcus aureus.

RSC Advances

Total synthesis of landomycins Q and R and related core structures for exploration of the cytotoxicity and antibacterial properties†

Abstract

Supplementary files

Article information

Download Citation

Permissions

Total synthesis of landomycins Q and R and related core structures for exploration of the cytotoxicity and antibacterial properties

Social activity

Search articles by author

Spotlight

Advertisements