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- Title
Short-step Synthesis of Cordytakaoamide B and Cordycepamide C via Intramolecular Regioselective Oxidation-Lactone Formation.
- Authors
Kasai, Yusuke; Ogawa, Takamitsu; Kawata, Mao; Tanigawa, Kana; Elshamy, Abdelsamed I.; Yoneyama, Tatsuro; Noji, Masaaki; Umeyama, Akemi; Imagawa, Hiroshi
- Abstract
The ortho -tyrosinol derivative, as a key synthetic intermediate for alkaloidal metabolites of Cordyceps, was synthesized from L-phenylalanine methyl ester via condensation with crotonic acid and oxidative intramolecular lactone formation by using phenyliodine(III) bis(trifluoroacetate). Subsequent elongation of the side chain involving a cross-metathesis reaction and deprotection yielded cordytakaoamide B and cordycepamide C in notably few synthetic steps. Furthermore, the S- configurations at the C-2 position of both cordytakaoamide B and cordycepamide C were confirmed by comparison with the sign of the optical rotation of the synthetic sample.
- Subjects
CROTONIC acid; CHEMICAL yield; CORDYCEPS; TRIFLUOROACETIC acid; ENTOMOPATHOGENIC fungi; OPTICAL rotation
- Publication
Natural Product Communications, 2022, Vol 17, Issue 5, p1
- ISSN
1934-578X
- Publication type
Article
- DOI
10.1177/1934578X221099141