Journal
TETRAHEDRON
Volume 74, Issue 34, Pages 4521-4529Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2018.07.025
Keywords
Dechlorogreensporone A; Dechlorogreensporone D; Resorcylic acid lactone; Total synthesis; Cytotoxic activity
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Funding
- Thailand Research Fund [TRG5880272]
- Center of Excellence for Innovation in Chemistry (PERCH-CIC), Office of the Higher Education Commission, Ministry of Education (OHEC)
- Graduate School, Prince of Songkla University
- Development and Promotion of Science and Technology Talents Project (DPST)
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The first and convergent total syntheses of polyketide natural products dechlorogreensporones A and D have been accomplished in 17 longest linear steps with 2.8% and 5.4% overall yields, respectively, starting from known methyl 2-(2-formyl-3,5-dihydroxyphenyl)acetate and commercially available R-(+)-propylene oxide and 1,2-epoxy-5-hexene. Our synthesis exploited key Mitsunobu esterification and (E) selective ring-closing metathesis (RCM) to assemble the macrocycles as well as a Jacobsen hydrolytic kinetic resolution to install the stereogenic centers. Both synthetic compounds were found to display significant cytotoxic activity against seven human cancer cell lines with the IC50 ranges of 6.66-17.25 mu M. (C) 2018 Elsevier Ltd. All rights reserved.
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