Synthesis and structural revision of annuionone A

Tetrahedron Letters

Volumn 44, Issue 37, 2003, Pages 7023-7025

  Takikawa, Hirosato ^a   Isono, Kazuhiko ^a   Sasaki, Mitsuru ^a   Macías, Francisco A ^b  

^a KOBE UNIVERSITY   (Japan)

^b UNIVERSITY OF CÁDIZ   (Spain)

Author keywords

Allelopathic agents; Oxy Michael addition; Sesquiterpenoids; Wacker oxidation

Indexed keywords

ANNUIONONE A; IONONE DERIVATIVE; PLANT EXTRACT; SESQUITERPENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; ISOLATION AND PURIFICATION; SUNFLOWER; SYNTHESIS;

HELIANTHUS;

EID: 0041657327     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01782-9     Document Type: Article

References (10)

1. Macías F.A., Varela R.M., Torres A., Oliva R.M., Molinillo J.M.G. Phytochemistry. 48:1997;631.
2. Macías F.A., Oliva R.M., Varela R.M., Torres A., Molinillo J.M.G. Phytochemistry. 52:1999;613.
3. Macías F.A., Torres A., Galindo J.L.G., Varela R.M., Álvarez J.A., Molinillo J.M.G. Phytochemistry. 61:2002;687.
4. Takikawa H., Hirooka M., Sasaki M. Tetrahedron Lett. 44:2003;5235-5238.
5. Liepa A.J., Wilkie J.S., Winzenberg K.N. Aust. J. Chem. 42:1989;1217.
6. Smidt J., Hafner W., Jira R., Sedlmeier J., Sieber R., Ruttinger R., Kojer H. Angew. Chem. 71:1959;176.
7. The following are the tested reaction conditions for the alkylation of 9 with 4-bromo-1-butene: LDA, THF, HMPA, -78°C to room temp.; KHMDS, 18-crown-6, THF, -78°C to room temp.
8. 2 gave 15 as the major product.
9. 3) δ=18.5, 20.7, 24.8, 30.0, 42.5, 43.4, 48.5, 49.3, 53.0, 78.2, 83.3, 207.4, 208.9
10. Macías and his co-workers have already reached the same conclusion independently: Macías, F. A.; López, A.; Varela, R. M. ; Torres, A.; Molinillo, J. M. G. Phytochemistry, 2003, submitted.