Synthesis of Acovenosides: Cardiac Glycosides with Potent Antitumor Activities
Acovenoside A (<b>1</b>), a cardiac glycoside featuring a unique l-acovenose at C-3 and a 1β,3β,14β-trihydroxy aglycone (namely, acovenosigenin A), shows promising antiproliferative activities. Herein, we report the synthesis of acovenoside A (<b>1</b>) together with a panel of its congeners. The synthesis features the stereoselective introduction of the 1β,14β-OH and C17-butenolide moieties starting from androstenedione (<b>7</b>) and gold(I)-catalyzed glycosylation with superarmed glycosyl <i>ortho</i>-alkynylbenzoates as donors.
Authors
- Peng Hui Xu (ORCID: https://orcid.org/0000-0002-9593-7167)
- Shuyang Bi
- Biao Yu (ORCID: https://orcid.org/0000-0002-3607-578X)
- Benzhang Liu
- Jing Wang (ORCID: https://orcid.org/0000-0001-7431-8925)
Institutions
- Shanghai Institute of Organic Chemistry (CN)
- University of Chinese Academy of Sciences (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-10-07
- DOI
- https://doi.org/10.1021/acs.orglett.4c03048
- Citations
- 5
- Primary Topic
- Carbohydrate Chemistry and Synthesis
- Type
- article
- Field-Weighted Citation Impact
- 1.25
Funders
- Mizutani Foundation for Glycoscience
- National Natural Science Foundation of China
- Chinese Academy of Sciences
- Science and Technology Commission of Shanghai Municipality
- Youth Innovation Promotion Association of the Chinese Academy of Sciences
- Opening Project of Shanghai Key Laboratory of New Drug Design