A synthesis of gombamide A (1) using N-terminal peptide extension, oxidative disulfide bond formation, and late-stage 4-hydroxystyrylamide installation has been achieved. This divergent method was also utilized to synthesize several gombamide A derivatives with modification to the 4-hydroxystyrylamide via cyclic peptide 2. The natural product and four derivatives were found to be devoid of Na(+)/K(+)-ATPase activity at 10 μM. In addition, the compounds were not cytotoxic at 10 μM against a panel of cancer cells.
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Construction of sulfur-containing moieties in the total synthesis of natural products.
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Shanghai Key Laboratory of Green Chemistry and Chemical Process, School of Chemistry and Molecular Engineering, East China Normal University, 3663 North Zhongshan Road, Shanghai 200062, P. R. China.
Covering: January 2013 to September 2018Sulfur-containing natural products are a large class of significant functional molecules. Many of these compounds exhibit potent biological activities and pharmacological properties; in fact, some of them have been developed into important drugs. The total synthesis of sulfur-containing natural products is a subject that has long attracted significant attention from synthetic organic chemists; to achieve this goal, various methods have been developed over the past years.
View Article and Find Full Text PDFDivergent Approach for the Synthesis of Gombamide A and Derivatives.
Org Lett
September 2016
Department of Pharmacological and Pharmaceutical Sciences, University of Houston, Science and Research Building 2, Room 549A, Houston, Texas 77204, United States.
A synthesis of gombamide A (1) using N-terminal peptide extension, oxidative disulfide bond formation, and late-stage 4-hydroxystyrylamide installation has been achieved. This divergent method was also utilized to synthesize several gombamide A derivatives with modification to the 4-hydroxystyrylamide via cyclic peptide 2. The natural product and four derivatives were found to be devoid of Na(+)/K(+)-ATPase activity at 10 μM.
View Article and Find Full Text PDFTotal Synthesis of Gombamide A.
Org Lett
August 2016
Departments of Chemistry and Pharmacology, Vanderbilt University, Nashville, Tennessee 37232, United States.
The first total synthesis of Gombamide A (1), a cytotoxic cyclic thiopeptide from the sponge Clathria gombawuiensis, has been achieved. Highlights of the convergent synthesis feature a disulfide bond forming cascade to close the 17-membered macrocycle and a selenoazidylation procedure to access the unusual para-hydroxystyrlyamide (pHSA) moiety. The synthesis required 18 steps, 11 steps in its longest linear sequence, and proceeded in 9.
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