Use of Flash Vacuum Thermolysis in a Stereocontrolled Synthesis of Optically Active Alkyl-substituted Cyclopentenones with Fragrant Properties
Binne Zwanenburg A B , Andries A. Volkers A and Antonius J. H. Klunder A
+ Author Affiliations
- Author Affiliations
A Radboud University Nijmegen, Institute for Molecules and Materials, Department of Organic Chemistry, Heyendaalseweg 135, 6525 AJ Nijmegen, The Netherlands.
B Corresponding author. Email: B.Zwanenburg@science.ru.nl
Australian Journal of Chemistry 67(9) 1234-1242 https://doi.org/10.1071/CH14093
Submitted: 25 February 2014 Accepted: 6 April 2014 Published: 26 May 2014
Abstract
The synthesis of four pairs of enantiopure antipodal substituted cyclopentenones is described. The synthetic sequences first comprise the preparation of a tricyclo[5.2.1.02,6]deca-4,8-dienone system, a subsequent kinetic enzymatic resolution of the appropriately functionalized tricyclic system, followed by a series of chemical transformations to install the desired substituents, and finally a retro Diels–Alder reaction using flash vacuum thermolysis to give the target products in high chemical and optical yields. The strategy makes effective use of the concept of transient chirality involving complete stereochemical control over reactions with the chiral tricyclic systems before thermal removal of the cyclopentadiene.
References
[1] P. L. Somogyi, Chem. Ind. 1996, 170.| 1:CAS:528:DyaK28XhsFGisb8%3D&md5=126265331aee9fe69a684571bebbffdeCAS |
[2] (a) J. E. Amoore, Perfum. Essent. Oil Rec. 1952, 43, 321.
| 1:CAS:528:DyaG3sXhtlygsg%3D%3D&md5=4ec3605e6054dd170007648a3f4ecbcdCAS |
(b) E. T. Theimer, Fragrance Chemistry, The Science of the Sense of Smell (Ed. E. T. Theimer) 2012 (Elsevier: Amsterdam).
[3] (a) A. Mosandl, Food Rev. Int. 1988, 4, 1.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL1cXhtlSisrg%3D&md5=d0f87cffb085f9c55ced0a23afebef58CAS |
(b) A. Mosandl, J. Chromatogr. A 1992, 624, 267.
| Crossref | GoogleScholarGoogle Scholar |
(c) M. Chastrette, C. Rognon, P. Sauvegrain, R. Amouroux, Chem. Senses 1992, 17, 555.
| Crossref | GoogleScholarGoogle Scholar |
(d) B. Koppenhoefer, R. Behnische, U. Epperlein, H. Holzschuh, Perfum. Flavor. 1994, 19, 1.
(e) M. H. Boelens, Perfum. Flavor. 1993, 18, 1.
[4] L. Friedman, J. G. Miller, Science 1971, 172, 1044.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE3MXksVCqtr0%3D&md5=b249eb36f185c3be1f0dd4f660693d5fCAS | 5573954PubMed |
[5] (a) H. Breer, in The Molecular Basics of Smell and Transduction, Ciba Foundation Symposium 179 (Ed. H. Breer) 1993, p. 97 (Wiley: Chichester).
(b) V. E. Dionne, A. E. Dubin, J. Exp. Biol. 1994, 194, 1.
(c) K. J. Rossiter, Chem. Rev. 1996, 96, 3201.
| Crossref | GoogleScholarGoogle Scholar |
[6] A. J. H. Klunder, J. Zhu, B. Zwanenburg, Chem. Rev. 1999, 99, 1163.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXisVGhtb0%3D&md5=aebb46c5091a26e6be386db58b9f0189CAS |
[7] (a) M. Revés, A. Lledó, Y. Li, E. Blasi, A. Riera, X. Verdaguer, Org. Lett. 2012, 14, 3534.
| Crossref | GoogleScholarGoogle Scholar | 22734894PubMed |
(b) L. N. Mander, R. J. Thomsons, J. Org. Chem. 2005, 70, 1654.
| Crossref | GoogleScholarGoogle Scholar |
(c) M. Iqbal, Y. Li, P. Evans, Tetrahedron 2004, 60, 2531.
| Crossref | GoogleScholarGoogle Scholar |
(d) J. P. Eddolls, M. Iqbal, S. M. Roberts, M. G. Santoro, Tetrahedron 2004, 60, 2539.
| Crossref | GoogleScholarGoogle Scholar |
(e) J. Christoffers, T. Werner, W. Frey, A. Baro, Chem. Eur. J. 2004, 10, 1042.
| Crossref | GoogleScholarGoogle Scholar |
(f) M. Iqbal, P. Evans, Tetrahedron Lett. 2003, 44, 5741.
| Crossref | GoogleScholarGoogle Scholar |
(g) T. J. Brocksom, J. Nakamura, M. L. Ferreira, U. Brocksom, J. Braz. Chem. Soc. 2001, 12, 597.
| Crossref | GoogleScholarGoogle Scholar |
(h) G. Mehta, D. S. Reddy, J. Chem. Soc., Perkin Trans. 1 2001, 1153.
| Crossref | GoogleScholarGoogle Scholar |
[8] (a) For some examples see: A. T. Levorse, R. A. Weiss, B. D. Newirth, (International Flavors & Fragrances Inc., USA), U.S. Pat. Appl. Publ. Cont.-in-part of U.S. Ser. No. 173,539, CODEN: USXXCO US 2007004608 A1 20070104 2007.
(b) A. T. Levorse, Jr, R. A. Weiss, B. D. Newirth, (International Flavors & Fragrances Inc., USA), U.S. Pat. Appl. Publ. CODEN: USXXAM US 7141699 B1 20061128 2006.
(c) K. Shimizu, (Asahi Kasei Chemicals Corporation, Japan), Jpn. Kokai Tokkyo Koho CODEN: JKXXAF JP 2006160690 A 20060622 2006.
(d) M. G. Monteleone, M. J. Clements, L. Croce, Jr, R. P. Belco, M. Pawla, (International Flavors & Fragrances Inc., USA), Eur. Pat. Appl. CODEN: EPXXDW EP 1609846 A1 20051228 2005.
(e) H. C. Hailes, in Special Publication–Royal Society of Chemistry, Advances in Flavours and Fragrances 2002, Vol. 277, pp. 127–137 (RSC: London).
(f) C. S. Letizia, J. Cocchiara, G. A. Wellington, C. Funk, A. M. Api, Food Chem. Toxicol. 2000, 38, S227.(Suppl.3)
| Crossref | GoogleScholarGoogle Scholar |
[9] A. J. H. Klunder, W. C. G. M. de Valk, J. M. J. Verlaak, J. W. M. Schellekens, J. H. Noordik, V. Parthasarathi, B. Zwanenburg, Tetrahedron 1985, 41, 963.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL2MXlslOqurg%3D&md5=997808033252ae269549f9564fc4bb83CAS |
[10] A. J. H. Klunder, W. B. Huizinga, A. J. M. Hulshof, B. Zwanenburg, Tetrahedron Lett. 1986, 27, 2543.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL2sXjslCq&md5=ba62567c0901421792fe513f5f91f03cCAS |
[11] (a) S. Takano, K. Inomata, K. Ogasawara, J. Chem. Soc. Chem. Commun. 1989, 271.
| 1:CAS:528:DyaK3cXnslej&md5=145d2bc620a1be1e862382a736dee924CAS |
(b) S. Takano, K. Inomata, M. Takahashi, K. Ogasawara, Synlett 1991, 636.
| Crossref | GoogleScholarGoogle Scholar |
[12] K. Tanaka, K. Ogasawara, Synthesis 1995, 1237.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2MXptlegu78%3D&md5=7bc72bfe49f66921454e30a44a1c6886CAS |
[13] (a) D. H. R. Barton, D. Crich, W. B. Motherwell, J. Chem. Soc. Chem. Commun. 1983, 939.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL2cXhtVeksb4%3D&md5=2084a87fb176986483bad38fe34ffa2fCAS |
(b) D. H. R. Barton, D. Crich, W. B. Motherwell, Tetrahedron 1985, 41, 3901.
| Crossref | GoogleScholarGoogle Scholar |
[14] (a) A. J. H. Klunder, A. A. Volkers, B. Zwanenburg, Tetrahedron 2009, 65, 2356.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXit1ais74%3D&md5=a31b2d3986559b3e29c4c914c16ff773CAS |
(b) A. A. Volkers, A. J. H. Klunder, B. Zwanenburg, Tetrahedron 2009, 65, 389.
| Crossref | GoogleScholarGoogle Scholar |
[15] J. Zhu, J. Van der Hoeven, J.-W. Slief, A. J. H. Klunder, B. Zwanenburg, Tetrahedron 1995, 51, 10953.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2MXosVahsrY%3D&md5=2b9dfe67564e5b27b4bd970c98d12eb4CAS |
[16] A. J. H. Klunder, B. Zwanenburg, in Gas Phase Reactions in Organic Synthesis (Ed. Y. Vallée) 1997, Ch. 2, pp. 107–142 (Gordon and Breach Science Publishers).
[17] A. J. H. Klunder, A. A. Volkers, B. Zwanenburg, Aust. J. Chem. 2014, 67, 1243.
| Crossref | GoogleScholarGoogle Scholar |
[18] J. Zhu, A. J. H. Klunder, B. Zwanenburg, Tetrathedron 1994, 50, 10597.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2MXos12lsw%3D%3D&md5=606ffa2620697df3134c0097f6410593CAS |
[19] S. Takano, M. Moriya, K. Tanaka, K. Ogasawara, Synthesis 1994, 687.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2cXmtlSgurg%3D&md5=a7ae020acb28e76623d745eb419dccd2CAS |
[20] J. Zhu, A. J. H. Klunder, B. Zwanenburg, Tetrahedron 1995, 51, 5099.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2MXlsFSlsbw%3D&md5=413a05b900b4f61c72c390f1229a9af3CAS |
