New synthesis of (11Z,13Z)-11,13-Hexadecadienal, the female sex pheromone of the navel orangeworm

Bioscience, Biotechnology and Biochemistry

Volumn 73, Issue 12, 2009, Pages 2727-2730

  Mori, Kenji ^a  

^a TOYO GOSEI CO LTD   (Japan)

Author keywords

(Z,Z) conjugated diene; Amyelois transitella; Hydroboration protonolysis; Pheromone; Sonogashira Hagihara coupling

Indexed keywords

1-DECANOL; AMYELOIS TRANSITELLA; BUILDING BLOCKES; FORMYL GROUP; HYDROBORATION; KEY REACTIONS; PROTONOLYSIS; SEX PHEROMONE;

BUTENES; HYDROCARBONS;

SYNTHESIS (CHEMICAL);

11 HEXADECENAL; 11-HEXADECENAL; ALDEHYDE; SEX PHEROMONE;

ANIMAL; ARTICLE; CHEMISTRY; FEMALE; LEPIDOPTERA; SYNTHESIS;

ALDEHYDES; ANIMALS; FEMALE; LEPIDOPTERA; SEX ATTRACTANTS;

AMYELOIS TRANSITELLA;

EID: 74549189427     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.90611     Document Type: Article

References (16)

1. Mori K, Tetrahedron, 65, 3900-3909 (2009).
2. Coffelt JA, Vick KW, Sonnet PE, and Doolittle RE, J. Chem. Ecol., 5, 955-966 (1979).
3. Higbee BS and Burks CS, J. Econ. Entomol., 101, 1633-1642 (2008).
4. Sonnet PE and Heath RR, J. Chem. Ecol., 6, 221-228 (1980).
5. Michelot D, Synthesis, 130-134 (1983).
6. Furber M and Taylor RJK, J. Chem. Soc., Perkin Trans. 1, 1809-1815 (1986).
7. Cabezas JA and Oehlschlager AC, Synthesis, 107-111 (1999).
8. Bishop CE and Morrow GW, J. Org. Chem., 48, 657-660 (1983).
9. Sonogashira K, Tohda Y, and Hagihara N, Tetrahedron Lett., 4467-4470 (1975).
10. Ratovelomana V and Linstrumelle G, Synth. Commun., 11, 917-923 (1981).
11. Mori K and Brevet J-L, Synthesis, 1125-1129 (1991).
12. Burger A, Clark JE, Nishimoto M, Muerhoff AS, Masters BSS, and Ortiz de Montellano PR, J. Med. Chem., 36, 1418-1424 (1993).
13. Plenio H, Angew. Chem. Int. ed., 47, 6954-6956 (2008).
14. Grodner J, Tetrahedron, 65, 1648-1654 (2009).
15. Hungerford NL and Kitching W, J. Chem. Soc., Perkin Trans. 1, 1839-1858 (1998).
16. Brown HC, "Organic Synthesis via Boranes," Wiley, New York, pp. 81-82 (1975).