Synthesis of heneicos-6(Z)-en-11-one, dec-5(Z)-en-l-yl acetate, dec-5(Z)-En-1-y1-3-methylbutanoate (insect sex pheromones)

Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry

Volumn 49, Issue 4, 2010, Pages 495-499

  Jindal, Rani ^a,b   Devi, Aarti ^a   Kad, Goverdhan L ^a   Singh, Jasvinder ^a  

^a PANJAB UNIVERSITY   (India)

^b SVCP ^*  (India)

Author keywords

Acetoxyhorohydride; Hydrohoration; Oxidation; Pheromones; Selective

Indexed keywords

EID: 77956079214     PISSN: 03764699     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (27)

1. Smith R G, Daterman G L & Daves G D, Jr Science, 188, 1975, 63.
2. Bestmann H J, Vostrowsky O, Koschatzhy K, Platz H, Brosck T, Kantardjiew I, Rhienwald M & Knawl W, Angew Chem Int Ed, 17, 1978, 768.
3. Willemse L P M, Booij C J H & Voermann S L, Angew Entomol, 103, 1987, 508.
4. Szocs G, Toth M & Novak L Z, Angew Entomol, 96, 1983, 56.
5. Henderson H E, Warren F L, Augustyn O P H, Burger B V, Schnider D F, Boschoff P R, Spies H S C & Geetsems H, J Chem Soc Chem Commun, 1972, 686.
6. (a) Smith R G & Daves G D, J Org Chem, 40, 1975, 1593;
7. (b) Kocienski P J & Cernigliaro G J, J Org Chem, 1976, 2927;
8. (c) Fentizon M & Lazare C, J Chem Soc Perkin Trans 1, 1978, 842.
9. Akermark B & Lyungyvist A, J Org Chem, 43, 1978, 4387.
10. Sharma M L, Verma S & Chand T, Indian J Chem, 34B, 2002, 1030.
11. White J & Whiteley C G, Synthesis, 1993, 1141.
12. Hayes J F, Shipman M & Twin H, J Org Chem, 67, 2002, 935.
13. Trehan I R, Singh J, Arora A K, Kaur J & Kad G L, Indian J Chem, 33B, 1994, 468.
14. (a) Konolew B G, Dzhumakulov T & Abduvakhabov A, Khim Prir Soedin, 1986, 122;
15. (b) Aurelia B A, Barabas A, Oprean I, Csonka H, Julianna & Honosan F, Rav Roum Chim, 28, 1983, 741;
16. (c) Odinokov V N, Balezina G G, Ishmuratov G, Yu Vakhitov R S H & Tolstikov G A, Khim Prir Soedin, 3, 1985, 395;
17. (d) Odinokov V N, Galeeva R I, Sokol's Kaya O V, Dzhemileva G A & Tolstikov G A, Dok Aka Nauk SSR, 280, 1985, 646;
18. (e) Yu Q T, Liu B N, Zang J Y & Haung Z H, Lipids, 23, 1988, 804.
19. Wenkert E, Ferrena V F, Michelotti E L & Tingoli M, J Org Chem, 50, 1985, 719.
20. Singh J, Sharma M, Kad G L & Kaur J, Indian J Chem, 46B, 2007, 2053.
21. Gautam V K, Singh J & Dhillon R S, J Org Chem, 53, 1988, 187.
22. Dhillon R S, Nayyar K & Singh J, Tetrahedron Lett, 33, 1992, 6015.
23. Caheiz G, Alexakis A & Normant J F, Tetrahedron Lett, 33, 1978, 3013.
24. Cornforth R H, Cornforth J W & Popjak G, Tetrahedron, 18, 1962, 1351.
25. (a) Lindlar H, Helv Chim Acta, 55, 1952, 446;
26. (b) Wadsworth W S & Emmons W D, J Am Chem Soc, 83, 1961, 1733.
27. Yadav J S, Upender V, Sekhran T & Reddy R E, Indian J Chem, 27B, 1988, 1012.