Journal
CHEMISTRY LETTERS
Volume 47, Issue 4, Pages 454-457Publisher
CHEMICAL SOC JAPAN
DOI: 10.1246/cl.171226
Keywords
Kaitocephalin; Chirality transfer; Sigmatropic rearrangement
Categories
Funding
- MEXT [26288018]
- Shorai Foundation for Science and Technology
- Grants-in-Aid for Scientific Research [15K05436, 26288018] Funding Source: KAKEN
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A stereoselective synthesis of kaitocephalin is described. The central strategy is based on chirality transfer reactions of three secondary alcohols derived from L-arabinose. The Overman rearrangement of an alpha, beta-unsaturated ester, and intramolecular anti-type S(Nu)2' reaction constructed a beta-hydroxy-alpha, alpha-disubstituted amino acid moiety. The third chirality transfer reaction is the Ichikawa rearrangement. These stereoselective reactions successfully established the three contiguous stereocenters embedded in kaitocephalin.
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