Synthesis of Spiro[4.5]decan-1-ones: A Formal Synthesis of Acoradienes and Related Sesquiterpenes via Rhodium-catalyzed Claisen Rearrangement/Hydroacylation

Synlett

Volumn 1996, Issue 12, 1996, Pages 1221-1223

  Sattelkau, Tim ^a   Hollmann, Christoph ^a   Eilbracht, Peter ^a  

^a TU DORTMUND UNIVERSITY   (Germany)

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[No Author keywords available]

Indexed keywords

EID: 1542499499     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5707     Document Type: Article

References (30)

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2. (b) P. Eilbracht, D. Lennartz, T. Huber, R. Meier, T. Sattelkau, unpublished results.
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11. For recent examples of spirocyclopentannulation: (a) A. Srikrishna, P. Praveen Kumar, R. Viswajanani, Tetrahedron Lett. 1996, 37, 1683-1686. (b) D.P. Provencal, J.W. Leahy, J. Org. Chem., 1994, 59, 5496-5498. (c) C. Kuroda, Y. Hirono, Tetrahedron Lett. 1994, 35, 6895-6896.
12. For recent examples of spirocyclopentannulation: (a) A. Srikrishna, P. Praveen Kumar, R. Viswajanani, Tetrahedron Lett. 1996, 37, 1683-1686. (b) D.P. Provencal, J.W. Leahy, J. Org. Chem., 1994, 59, 5496-5498. (c) C. Kuroda, Y. Hirono, Tetrahedron Lett. 1994, 35, 6895-6896.
13. For recent examples of spirocyclopentannulation: (a) A. Srikrishna, P. Praveen Kumar, R. Viswajanani, Tetrahedron Lett. 1996, 37, 1683-1686. (b) D.P. Provencal, J.W. Leahy, J. Org. Chem., 1994, 59, 5496-5498. (c) C. Kuroda, Y. Hirono, Tetrahedron Lett. 1994, 35, 6895-6896.
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19. Compound 9a: G.A. Molander, J.A. McKie, J. Org. Chem. 1993, 58, 7216-7227.
20. 18O (166.26) C:79.5 H:10.9, Found: C:79.7 H:11.4.
21. tbutyl-ether 8:1). In the case of product 10 the solvent could partially be removed by Kugelrohr-distillation prior to chromatography.
22. V.N. Gramenitskaya, I.S. Golovkina, V.S. Orach, N.S. Vul'fson, J. Org. Chem. USSR (Engl. Transl.) 1975, 11, 978-983.
23. ++1], 161(22), 123(100), 105(28), 95(90), 81(40), 67(26); IR(NaCl,film): ṽ = 3014(w), 2962(s), 2911(vs,br), 2856(s), 1689(s), 1672(w), 1447(m), 1154(vs), 1145(vs), 1116(vs), 966(s).
24. K.C. Brannock, J. Am. Chem. Soc. 1959, 81, 3379-3382.
25. +) calcd 178.1358, found 178.1358, IR(NaCl,film): ṽ= 3012(w), 2961(s), 2927(s), 1736(vs), 1450(m), 1149(m), 803(m).
26. 13C-COSY spectra. The relative structures of the diastereoisomers of 2 were assigned with NOESY spectra. See S. Braun, H.-O. Kalinowski, S. Berger, 100 and More Basic NMR Experiments, VCH: Weinheim; New York, 1996 and references cited therein.
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30. (b) T. Huber, P. Eilbracht, unpublished results.