Total synthesis of thioamycolamide A using diastereoselective sulfa-Michael addition as the key step

Yi Xiao, Yangyang Jiang, Chao Xu, Pratanphorn Nakliang, Sanghee Yoon, Sun Choi, Yian Guo, Tao Ye

Research output: Contribution to journalArticlepeer-review

Abstract

The stereocontrolled total synthesis of the antitumor natural product thioamycolamide A has been accomplished in 14 longest linear steps and an overall yield of 19.1%. The central feature of our convergent route to this family of novel macrocyclic natural products is the preparation of the β-alkylthio amide subunit through an auxiliary-controlled, diastereoselective sulfa-Michael addition.

Original languageEnglish
Pages (from-to)3998-4002
Number of pages5
JournalOrganic Chemistry Frontiers
Volume9
Issue number15
DOIs
StatePublished - 14 Jun 2022

Bibliographical note

Funding Information:
We acknowledge financial support from the National Natural Science Foundation of China (21772009), (21901013), the Shenzhen Peacock Plan (KQTD2015071714043444), the Shenzhen Science and Technology Innovation Commission (JCYJ20170818090017617), the Guangdong Natural Science Foundation (2014B030301003 and 2021A1515010344), and the Foundation of Guangdong Department of Education (2021ZDJS097). This work was also supported by the Mid-career Researcher Program (NRF-2020R1A2C2101636), the Medical Research Center (MRC) grant (NRF-2018R1A5A2025286), the Brain Pool Program (NRF-2020H1D3A1A02080803), and the Bio & Medical Technology Development Program (NRF-2019M3E5D4065251) funded by the Ministry of Science and ICT (MSIT) and the Ministry of Health and Welfare (MOHW) through the National Research Foundation of Korea (NRF) and Peng Cheng Scholar (to S. C.). We also thank the Korea Institute of Science and Technology Information (KISTI) Supercomputing Center for providing computing resources (KSC-2020-INO-0010) and the Ewha Womans University Research Grant of 2021 (to S. C.). This work was also inspired by the International and Interdisciplinary Environments of the JSPS Asian CORE Program, “Asian Chemical Biology Initiative”.

Publisher Copyright:
© 2022 The Royal Society of Chemistry.

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