RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
PDF herunterladen
Synthesis 2013; 45(11): 1513-1518
DOI: 10.1055/s-0033-1338432
DOI: 10.1055/s-0033-1338432
paper
A Practical Total Synthesis of Both E- and Z-Isomers of Optically Pure (S)-14-Methylhexadec-8-enal (Trogodermal)
Authors
Weitere Informationen
Publikationsverlauf
Received: 22. Januar 2013
Accepted after revision: 28. März 2013
Publikationsdatum:
08. Mai 2013 (online)
Abstract
The total synthesis of both E- and Z-isomers of optically pure (S)-14-methylhexadec-8-enal (trogodermal) is described. Key steps involved Corey–Fuchs reaction, zipper isomerization, and different hydrogenation conditions for cis- and trans-isomers.
-
References
- 1a Rodin JO, Silverstein RM, Burkholder WE, Gorman JE. Science (Washington, D.C) 1969; 165: 904
- 1b Silverstein RM, Cassidy RF, Burkholder WE, Shapas TJ, Levinson HZ, Levinson AR, Mori K. J. Chem. Ecol. 1980; 6: 911
- 1c Cross JH, Byler RC, Cassidy RF. Jr, Silverstein RM, Greenblatt RE, Burkholder WE, Levinson AR, Levinson HZ. J. Chem. Ecol. 1976; 2: 457
- 2a Mori K. Tetrahedron Lett. 1973; 14: 3869
- 2b Mori K. Tetrahedron 1974; 30: 3817
- 2c Mori K, Suguro T, Uchida M. Tetrahedron 1978; 34: 3119
- 2d Suguro T, Mori K. Agric. Biol. Chem. 1979; 43: 409
- 2e Mori K, Kuwahara S, Levinson HZ, Levinson AR. Tetrahedron 1982; 38: 2291
- 2f Mori K. Tetrahedron 2009; 65: 3900
- 3a Rossi R, Carpita A. Tetrahedron 1977; 33: 2447
- 3b Rossi R, Salvadori PA, Carpita A, Niccoli A. Tetrahedron 1979; 35: 2039
- 3c Rossi R, Niccoli A. Naturwissenschaften 1978; 65: 259
- 4a Chattopadhyay S, Mamdapur VR, Chadha MS. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1989; 28: 848
- 4b Chattopadhyay S, Mamdapur VR, Chadha MS. Synth. Commun. 1990; 20: 825
- 5a Yadav JS, Uma Gayathri K, Thrimurtulu N, Prasad AR. Tetrahedron 2009; 65: 3536
- 5b Yadav JS, Jagan Reddy E, Ramalingam T. New J. Chem. 2001; 25: 223
- 5c Yadav JS, Madabushi YV, Prasad AR. Tetrahedron 1998; 54: 7551
- 5d Yadav JS, Reddy KV, Chandrashekar S. Synth. Commun. 1998; 28: 4249
- 6a Corey EJ, Fuchs PL. Tetrahedron Lett. 1972; 13: 3769
- 6b Gibtner T, Hampel F, Gisselbrecht JP, Hirsch A. Chem. Eur. J. 2002; 8: 408
- 6c Mori M, Tonogaki K, Kinoshita A. Org. Synth. 2005; 81: 1
- 6d Desai NB, Mckelvie N. J. Am. Chem. Soc. 1962; 84: 1745
- 7a Macaulay SR. Can. J. Chem. 1980; 58: 2567
- 7b Trost BM, Horne DB, Woltering MJ. Chem. Eur. J. 2006; 12: 6607
- 7c Brown CA, Yamashita A. J. Am. Chem. Soc. 1975; 97: 891
- 7d Kimmel T, Becker D. J. Org. Chem. 1984; 49: 2494
- 7e Hoye RC, Baigorria AS, Danielson ME, Pragman AA, Rajapakse HA. J. Org. Chem. 1999; 64: 2450
- 7f Rama Rao AV, Ravindra Reddy G. Tetrahedron Lett. 1993; 34: 8329
- 7g Sabitha G, Yadagiri K, Yadav JS. Tetrahedron Lett. 2007; 48: 1651
- 7h Yadav JS, Chandrasekhar S, Rajashaker K. Synth. Commun. 1995; 25: 4035
- 7i Kirkham JE. D, Courtney TD. L, Lee V, Baldwin JE. Tetrahedron Lett. 2004; 45: 5645
- 7j Hass EC, Mezey PG, Abrams SR. J. Comput. Chem. 1982; 3: 185
- 8 Yadav JS, Venkatesh M, Thrimurtulu N, Prasad AR. Synlett 2010; 1255