- Integration of CiNii Books functions for fiscal year 2025 has completed
- Trial version of CiNii Research Knowledge Graph Search feature is available on CiNii Labs
- 【Updated on November 26, 2025】Regarding the recording of “Research Data” and “Evidence Data”
- Start the collection of all publicly IRDB content
- Incorporate Research Data from KAKEN
First Total Synthesis of Antimitotic Compound, (+)-Phomopsidin
-
- Takahiro Suzuki
- Department of Chemistry, School of Science and Engineering, Waseda University, 3-4-1 Ohkubo, Shinjuku-ku, Tokyo 169-8555, Japan, and Department of Ocean Sciences, Tokyo University of Marine Science and Technology, Minato-ku, Tokyo 108-8477, Japan
-
- Kenji Usui
- Department of Chemistry, School of Science and Engineering, Waseda University, 3-4-1 Ohkubo, Shinjuku-ku, Tokyo 169-8555, Japan, and Department of Ocean Sciences, Tokyo University of Marine Science and Technology, Minato-ku, Tokyo 108-8477, Japan
-
- Yoshiharu Miyake
- Department of Chemistry, School of Science and Engineering, Waseda University, 3-4-1 Ohkubo, Shinjuku-ku, Tokyo 169-8555, Japan, and Department of Ocean Sciences, Tokyo University of Marine Science and Technology, Minato-ku, Tokyo 108-8477, Japan
-
- Michio Namikoshi
- Department of Chemistry, School of Science and Engineering, Waseda University, 3-4-1 Ohkubo, Shinjuku-ku, Tokyo 169-8555, Japan, and Department of Ocean Sciences, Tokyo University of Marine Science and Technology, Minato-ku, Tokyo 108-8477, Japan
-
- Masahisa Nakada
- Department of Chemistry, School of Science and Engineering, Waseda University, 3-4-1 Ohkubo, Shinjuku-ku, Tokyo 169-8555, Japan, and Department of Ocean Sciences, Tokyo University of Marine Science and Technology, Minato-ku, Tokyo 108-8477, Japan
Bibliographic Information
- Published
- 2004-01-16
- DOI
-
- 10.1021/ol036338q
- 10.1002/chin.200426186
- Publisher
- American Chemical Society (ACS)
Search this article
Description
[reaction: see text] The first total synthesis of (+)-phomopsidin has been achieved via a diastereoselective transannular Diels-Alder (TADA) reaction. Key steps in the synthesis include diastereoselective ynone reduction with (-)-alpha-pinene and 9-BBN, macrocyclization by E-selective intramolecular Horner-Wadsworth-Emmons (HWE) reaction, as well as carbometalation under Wipf's conditions, followed by HWE reaction at low temperature to selectively construct the (E)-1-methylpropenyl and (1E,2E)-4-carboxy-1,3-butadienyl substituents.
Journal
-
- Organic Letters
-
Organic Letters 6 (4), 553-556, 2004-01-16
American Chemical Society (ACS)