Synthesis of Tetrahydropyran/Tetrahydrofuran-Containing Macrolides by Palladium-Catalyzed Alkoxycarbonylative Macrolactonizations†
Yu Bai
Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, IN 47907 (USA) http://www.chem.purdue.edu/dai/
Search for more papers by this authorDexter C. Davis
Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, IN 47907 (USA) http://www.chem.purdue.edu/dai/
Search for more papers by this authorCorresponding Author
Prof. Dr. Mingji Dai
Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, IN 47907 (USA) http://www.chem.purdue.edu/dai/
Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, IN 47907 (USA) http://www.chem.purdue.edu/dai/Search for more papers by this authorYu Bai
Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, IN 47907 (USA) http://www.chem.purdue.edu/dai/
Search for more papers by this authorDexter C. Davis
Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, IN 47907 (USA) http://www.chem.purdue.edu/dai/
Search for more papers by this authorCorresponding Author
Prof. Dr. Mingji Dai
Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, IN 47907 (USA) http://www.chem.purdue.edu/dai/
Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, IN 47907 (USA) http://www.chem.purdue.edu/dai/Search for more papers by this authorWe thank Professor Yu Xia’s group at Purdue University for mass spectrometric assistance, the NYU Molecular Design Institute for the purchase of the Bruker SMART APEXII Diffractometer, and Dr. Chunhua Hu for his assistance with data collection and structure determination. Financial support from the Purdue University and Purdue Center for Cancer Research is gratefully acknowledged. We thank the NIH P30CA023168 for supporting shared resources to Purdue University Center for Cancer Research. Y.B. thanks the Purdue Research Foundation for a research assistantship and D.C.D. thanks the H. C. Brown Funds for a summer research support. M.D. is a recipient of the 2013 Showalter Research Trust Award and 2013 ORAU Ralph E. Powe Junior Faculty Enhancement Award.
Graphical Abstract
CO for bridged macrolides: An efficient Pd-catalyzed cascade alkoxycarbonylative macrolactonization to synthesize various THP/THF-containing macrolactones in one step from relatively simple alkendiols is possible. Challenging macrolactones involving tertiary alcohols were synthesized smoothly as well. The method was applied to the synthesis of the potent anticancer compound 9-demethylneopeltolide.
Abstract
A novel Pd-catalyzed cascade alkoxycarbonylative macrolactonization to construct tetrahydropyran/tetrahydrofuran-containing bridged macrolactones in one step from alkendiols is described. Products with various ring sizes and substituents were obtained. Challenging macrolactones involving tertiary alcohols were synthesized smoothly as well. Mechanistically, experimental evidence to support a trans-oxypalladation step has been provided. The method was applied to the synthesis of potent anticancer compound 9-demethylneopeltolide.
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