Synthesis of the ABC ring system of jiadifenin via pd-catalyzed cyclizations

Organic Letters

Volumn 13, Issue 5, 2011, Pages 988-991

  Harada, Kenichi ^a   Imai, Akiko ^a   Uto, Kazuharu ^a   Carter, Rich G ^c   Kubo, Miwa ^a   Hioki, Hideaki ^b   Fukuyama, Yoshiyasu ^a  

^a TOKUSHIMA BUNRI UNIVERSITY   (Japan)

^b GUNMA UNIVERSITY   (Japan)

^c OREGON STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

JIADIFENIN; PALLADIUM; SESQUITERPENE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; SYNTHESIS;

CATALYSIS; CYCLIZATION; MOLECULAR STRUCTURE; PALLADIUM; SESQUITERPENES;

EID: 79952175773     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol103024z     Document Type: Article

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27. The identity of which diastereomer corresponds to the 5 R * and 5 S * stereochemistries is based on the correlation to the observed Tsuji-Trost products.
28. The reaction did not proceed in relatively nonpolar solvents such as toluene and THF. Using more polar solvents such as DMF and DMSO, preferential O -alkylation (over C -alkylation) of β-ketoester was observed.
29. This structure was confirmed by X-ray crystallographic analysis. See Supporting Information for full details.
30. Although these conditions used (R)-BINAP, the same results were observed using (±)-BINAP.