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Synfacts 2009(7): 0703-0703
DOI: 10.1055/s-0029-1217242
DOI: 10.1055/s-0029-1217242
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of Nakiterpiosin
Contributor(s):Philip KocienskiS. Gao, Q. Wang, C. Chen*
The University of Texas Southwestern Medical Center at Dallas, USA
Synthesis and Structure Revision of Nakiterpiosin
J. Am. Chem. Soc. 2009, 131: 1410-1412
The University of Texas Southwestern Medical Center at Dallas, USA
Synthesis and Structure Revision of Nakiterpiosin
J. Am. Chem. Soc. 2009, 131: 1410-1412
Further Information
Publication History
Publication Date:
22 June 2009 (online)
Key words
nakiterpiosin - photo-Nazarov cyclization - carbonylative cross-coupling - Diels-Alder reaction
Significance
The synthesis of nakiterpiosin, a cytotoxic sponge metabolite, features a Pd-catalyzed carbonylative cross-coupling (K → L) followed by a photo-Nazarov cyclization (L → M) to create the indanone moiety.
Comment
The photo-Nazarov cyclization entails a thermal electrocyclization induced by photoisomerization of the enone L. Lewis acid cataly-zed variants were too harsh. CuCl and DMSO dramatically enhanced the rate of the cross-coupling K → L.