Syntheses of Aggregation Pheromones
of the Palm Weevils Rhyncophorus vulneratus and R. phoenicis and of (+)-trans-Whiskey Lactone

J. S. Yadav; C. Venkateshwar Rao; A. R. Prasad; Ahmad Al Khazim Al Ghamdi

doi:10.1055/s-0031-1289579

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Synthesis 2011(23): 3894-3898
DOI: 10.1055/s-0031-1289579

PAPER

Syntheses of Aggregation Pheromones of the Palm Weevils Rhyncophorus vulneratus and R. phoenicis and of (+)-trans-Whiskey Lactone

J. S. Yadav*^a,b, C. Venkateshwar Rao^a, A. R. Prasad^a, Ahmad Al Khazim Al Ghamdi^b
^a Division of Organic Chemistry I, CSIR, Indian Institute of Chemical Technology, Hyderabad, 500 007, India
^b Engineer Abdullah Baqshan for Bee Research, King Saud University, Saudi Arabia
Fax: +91(40)27160512; e-Mail: yadav@iict.res.in;

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Publication History

Received 6 August 2011
Publication Date:
27 October 2011 (online)

Abstract
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Abstract

(3S,4S)-3-Methyloctan-4-ol, (4S,5S)-4-methylnonan-5-ol, and (+)-trans-whiskey lactone [(4S,5R)-5-butyl-4-methyldihydrofuran-2(3H)-one] were synthesized stereoselectively by using a radical cyclization reaction as a key step. All three molecules were synthesized from a common cyclic acetal intermediate.

Key words

alcohols - pheromones - lactones - radical reactions - stereoselective synthesis

References

1 Rochat D. Malosse C. Lettere M. Ramirez-Lucas P. Einhorn J. Zagatti P. C. R. Acad. Sci., Ser. II 1993, 316: 1737

Google Scholar
2 Mori K. Kiyota H. Rochat D. Liebigs Ann. Chem. 1993, 865

Google Scholar
3 Weissling TJ. Giblin-Davis RM. Gries G. Perez AL. Pierce HD. Oehlschlager AC. J. Chem. Ecol. 1994, 20: 505

Google Scholar
5a Mori K. Kiyota H. Malosse C. Rochat D. Liebigs Ann. Chem. 1993, 1201

Google Scholar
5b Mori K. Murata N. Liebigs Ann. 1995, 697

Google Scholar
6 Odriozola MJ. Garcia MJ. González A. Gil P. Tetrahedron: Asymmetry 1999, 10: 4627

Google Scholar
7a Ohloff G. Fortschr. Chem. Org. Naturst. 1978, 35: 431

Google Scholar
7b Ho T.-l. Synth. Commun. 1983, 13: 341

Google Scholar
8a Brand JM. Young JC. Silverstein RM. Fortschr. Chem. Org. Naturst. 1979, 37: 1

Google Scholar
8b Mori K. Ebata T. Takechi S. Tetrahedron 1984, 40: 1761

Google Scholar
9a Otsuka K. Zenibayashi Y. Itoh M. Totsuka A. Agric. Biol. Chem. 1974, 50: 485 ; and references cited therein

Google Scholar
9b Masuda M. Nishimura K. Chem. Lett. 1981, 1333

Google Scholar
10a Marino JP. de la Pradilla RF. Tetrahedron Lett. 1985, 26: 5381

Google Scholar
10b Gunther C. Mosandl A. Liebigs Ann. Chem. 1986, 12: 2112

Google Scholar
10c Beckmann M. Hildebrandt H. Winterfeldt E. Tetrahedron: Asymmetry 1990, 1: 335

Google Scholar
10d Sharma GV. Vepachedu SR. Chandrasekhar S. Synth. Commun. 1990, 20: 3403

Google Scholar
10e Miata O. Shinada T. Kawakami N. Taji K. Ninomiya I. Naito T. Date T. Okamura K. Chem. Pharm. Bull. 1992, 40: 2579

Google Scholar
10f Zschage O. Hoppe D. Tetrahedron 1992, 48: 5657

Google Scholar
10g Ebata T. Matsumoto K. Yoshikoshi H. Koseki K. Kawakami H. Okano K. Matsushita H. Heterocycles 1993, 36: 1017

Google Scholar
10h Katsuji I. Yoshitake M. Katsuki T. Tetrahedron 1996, 52: 3905

Google Scholar
10i Hisashi N. Katsuji I. Tsutomu K. Tetrahedron: Asymmetry 1998, 9: 1165

Google Scholar
11a Bloch R. Gilbert L. J. Org. Chem. 1987, 52: 4603

Google Scholar
11b Taber DF. Houze JB. J. Org. Chem. 1994, 59: 4004

Google Scholar
11c Pai Y.-C. Fang J.-M. Wu S.-H. J. Org. Chem. 1994, 59: 6018

Google Scholar
11d Takahata H. Uchida Y. Momose T. Tetrahedron Lett. 1994, 35: 4123

Google Scholar
11e Takahata H. Uchida Y. Momose T. J. Org. Chem. 1995, 60: 5628

Google Scholar
12a Yadav JS. Jagan Reddy E. Ramalingam T. New J. Chem. 2001, 25: 223

Google Scholar
12b Yadav JS. Valli MY. Prasad AR. Tetrahedron 1998, 54: 7551

Google Scholar
12c Yadav JS. Reddy KV. Chandrashekar S. Synth. Commun. 1998, 28: 4249

Google Scholar
12d Yadav JS. Deshpande PK. Tetrahedron 1992, 48: 4465

Google Scholar
12e Yadav JS. Rao ES. Synth. Commun. 1989, 19: 705

Google Scholar
12f Yadav JS. Deshpande PK. Reddy ER. Synth. Commun. 1989, 19: 125

Google Scholar
13 Gao Y. Klunder JM. Hanson RM. Masamune H. Ko SY. Sharpless KB. J. Am. Chem. Soc 1987, 109: 5765

Google Scholar
14 Garegg PJ. Samuelson B. J. Chem. Soc., Perkin Trans. 1 1980, 2866

Google Scholar
15 Ueno Y. Moriya O. Chino K. Watanabe M. Okwara M. J. Chem. Soc., Perkin Trans. 1 1986, 1351

Google Scholar
16 Nicolaou KC. Duggan ME. Ladduwahetty J. Tetrahedron Lett. 1984, 25: 2069

Google Scholar
17a Yadav JS. Gadgil VR. J. Chem. Soc., Chem. Commun. 1989, 23: 1824

Google Scholar
17b Stork G. Mook R. Biller SA. Rychnovsky SD. J. Am. Chem. Soc. 1983, 105: 3741

Google Scholar
17c Baldwin JE. J. Chem. Soc., Chem. Commun. 1976, 734

Google Scholar
18 Mitsunobu O. Synthesis 1981, 1

Google Scholar
19 Seebach D. Corey EJ. J. Org. Chem. 1975, 40: 231

Google Scholar
20 Fujisawa T. Mobele IB. Shimizu M. Tetrahedron Lett. 1992, 33: 5567

Google Scholar
21 Suzuki H. Tanaka A. Yamashita K. Agric. Biol. Chem. 1987, 3369

Google Scholar

4

Perez A. L., Gries R., Gries G., Hallett R. H., Oehlschlager A. C., Pierce H. D. Jr., Gonzalez L. M., Borden J. H., Giblin-Davis R. M.; In Abstracts of Papers, Tenth Annual Meeting of the International Society of Chemical Ecology, Tampa, FL (USA), July 31-August 4, 1993; p. 54.