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Communication
The Total Synthesis of Heliquinomycinone
Article first published online: 18 DEC 2001
DOI: 10.1002/1521-3773(20011217)40:24<4713::AID-ANIE4713>3.0.CO;2-N
© 2001 WILEY-VCH Verlag GmbH, Weinheim, Fed. Rep. of Germany
Issue
40:24<>1.0.CO;2-C/asset/cover.gif?v=1&s=b08f9faa7111269bc0c4a09514fd225adbce638b "Angewandte Chemie International Edition")
Angewandte Chemie International Edition
Volume 40, Issue 24, pages 4713–4716, December 17, 2001
Additional Information
How to Cite
Siu, T., Qin, D. and Danishefsky, S. J. (2001), The Total Synthesis of Heliquinomycinone . Angewandte Chemie International Edition, 40: 4713–4716. doi: 10.1002/1521-3773(20011217)40:24<4713::AID-ANIE4713>3.0.CO;2-N
Publication History
- Issue published online: 18 DEC 2001
- Article first published online: 18 DEC 2001
- Manuscript Received: 5 SEP 2001
- Abstract
- Article
- References
- Cited By
Keywords:
- antitumor agents;
- dihydroxylation;
- quinones;
- spiro compounds;
- total synthesis
Graphical Abstract
40:24<4713::AID-ANIE4713>3.0.CO;2-N/asset/image_m/mcontent.gif?v=1&s=5dc072a47fe5b97fdf881bd1e41ed4679387c758 "Thumbnail image of graphical abstract")
A strategy for the synthesis of heliquinomycin, a selective helicase inhibitor, hinges on the spirocyclization of precursor 3. Naphthofuran 1 and aldehyde 2 were readily prepared and used in the synthesis of 3. The key steps in the total synthesis of heliquinomycinone (4) include the regioselective dihydroxylation of 3, and a novel spirocyclization under Mitsunobu conditions.