Journal
HETEROCYCLES
Volume 89, Issue 1, Pages 127-142Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.3987/COM-13-12880
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Funding
- JSPS KAKENHI [22404006]
- Global COE Program for Chemistry Innovation
- University of Tokyo
- NOAA-ECOHAB [MML-106390A]
- NCDHHS [01515-04]
- Grants-in-Aid for Scientific Research [22404006] Funding Source: KAKEN
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Proposed biosynthetic intermediates of a marine monocyclic ether alkaloid, brevisamide (1) were synthesized for biosynthetic studies on the marine ladder-frame polyethers. The intermediates comprising a linear backbone with trans-olefin (2) and epoxide (3) functionality were synthesized via a Suzuki-Miyaura cross coupling reaction and a Katsuki Sharpless asymmetric epoxidation reaction. In protic solvents, 3 was unstable and readily cyclized to an unnatural 5-membered ether ring compound (4).
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