Chiral arene-Cr(CO)3 complexes in organic synthesis: A short enantioselective total synthesis of putative helioporin D

Tetrahedron Letters

Volumn 39, Issue 12, 1998, Pages 1537-1540

  Geller, Thomas ^a   Schmalz, Hans Günther ^a   Bats, Jan W ^b  

^a TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

^b GOETHE UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

DITERPENE; HELIOPORIN D; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CHIRALITY; CRYSTAL STRUCTURE; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0032546283     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00021-5     Document Type: Article

References (29)

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19. 23 = -15.4° (c = 5.0 in EtOH)) was prepared from rac-7 by enzymatic resolution using porcine pancreas lipase following the protocol of Stokes and Oehlschlager: Stokes, T. M., Oehlschlager, A.C. Tetrahedron Lett. 1987, 28, 2091.
20. 9. This compound was shown to be the epimer of 9 at the sidechain chirality center as it evolved as the (slightly) dominating product on alkylation of 6 with rac-8 (d.s.: 2 : 3).
21. 10. Stang, P.J.; Hanack, M.; Subramanian, L.R. Synthesis 1982, 85.
22. 3): δ * 13.6 (q), 15.7 (t), 17.7 (q), 19.9 (q), 25.7 (q), 25.9 (t), 27.4 (t), 28.0 (d), 34.5 (t), 37.0 (d), 38.7 (d), 55.9 (q), 65.6 (q), 74.5 (d), 89.4 (d), 105.3 (s), 117.0 (s), 124.1 (d), 128.7 (s), 131.9 (s), 134.3 (s), 234.6 (s).
23. w = 0.042. Crystallographic data (excluding structure factors ) for rac-10 have been deposited with the Cambridge Crystatlographic Data Centre as supplementary publication no. CCDC-100864, Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: Int. code +(1223)336-033; e-mail: teched@ccdc.cam.ac.uk).
24. 3): δ = 13.8 (q), 15.6 (t), 16.0 (q), 17.7 (q), 20.0 (q), 25.7 (q), 26.0 (t), 27.6 (d), 28.0 (t), 34.6 (t), 37.2 (d), 38.7 (d), 62.2 (q), 63.2 (q), 88.4 (d), 103.1 (s), 109.8 (s), 111.2 (s), 124.1 (d), 131.2 (s), 131.8 (s), 135.4 (s), 234.3 (s).
25. 14. LiSEt was prepared from HSEt and nBuLi in hexane followed by solvent evaporation; for details, see: T. Geller, Dissertation, TU-Berlin, 1997. For the use of LiSMe for the cleavage of mono-methoxyarenes, see: T. Ross Kelly, H. M. Dali, W.-G. Tsang, Tetrahedron Lett. 1977, 3859.
26. 14. LiSEt was prepared from HSEt and nBuLi in hexane followed by solvent evaporation; for details, see: T. Geller, Dissertation, TU-Berlin, 1997. For the use of LiSMe for the cleavage of mono-methoxyarenes, see: T. Ross Kelly, H. M. Dali, W.-G. Tsang, Tetrahedron Lett. 1977, 3859.
27. 15. Clark, J.H.; Holland, H.L., Miller, J.M. Tetrahedron Lett. 1976, 3361.
28. 3): δ = 14.4 (q), 14.7 (q), 17.7 (t), 17.7 (q), 20.5 (q), 25.8 (q), 26.3 (t), 27.2 (d), 28.5 (t), 35.1 (t), 35.7 (d), 41.1 (d), 100.5 (t), 116.2 (s), 121.6 (d), 123.3 (s), 124.8 (d), 131.3 (s), 133,3 (s), 142.7 (s), 144.4 (s).
29. 17. Geller, T.; Jakupovic, J.; Schmalz, H.-G. Tetrahedron Lett, 1998, 39, 1541.