Total Syntheses of 3-epi-Litsenolide D2 and Lincomolide A
- Noriki Kutsumura*Noriki Kutsumura*E-mail: [email protected]International Institute for Integrative Sleep Medicine (WPI-IIIS), University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8575, JapanDepartment of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, JapanMore by Noriki Kutsumura,
- Akito KirisekoAkito KirisekoDepartment of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, JapanMore by Akito Kiriseko,
- Kentaro NiwaKentaro NiwaDepartment of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, JapanMore by Kentaro Niwa, and
- Takao Saito*Takao Saito*E-mail: [email protected]Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, JapanMore by Takao Saito
Abstract
The first total syntheses of 3-epi-litsenolide D2 and its enantiomer lincomolide A were achieved. The synthetic highlights of our approach include olefin cross metathesis and bromine addition to the generated double bond, followed by the regioselective HBr-elimination and intramolecular carbonylation using bis(triphenylphosphine)dicarbonylnickel. This investigation also revealed that the previously reported specific optical rotation of 3-epi-litsenolide D2 should be revised.
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