Highly Diastereoselective Conjugate Addition of Lithiated γ-Crotonolactone (But-2-en-4-olide) to Cyclic Enones to Give Syn-Adducts: Application to a Brefeldin Synthesis

Journal of Organic Chemistry

Volumn 62, Issue 14, 1997, Pages 4552-4553

  Haynes, Richard K ^a   Lam, William W L ^a   Yeung, Lam Lung ^a   Williams, Ian D ^a   Ridley, Andrew C ^b   Starling, Scott M ^b   Vonwiller, Simone C ^b   Hambley, Trevor W ^b   Lelandais, Patrick ^c,d  

^a HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

^b UNIVERSITY OF SYDNEY   (Australia)

^c UNIVERSITY OF GENEVA   (Switzerland)

^d Email:   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

BREFELDIN A; BUTENOLIDE; LITHIUM DERIVATIVE;

CHEMICAL BOND; CONJUGATE; DIASTEREOISOMER; DRUG SYNTHESIS; ISOMERISM; NOTE; STEREOCHEMISTRY;

EID: 0030876791     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970337s     Document Type: Article

References (31)

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2. Binns, M. R.; Haynes, R. K.; Katsifis, A. G.; Schober, P. A.; Vonwiller, S. C. J. Am. Chem. Soc. 1988, 111, 5411. Oare, D. H.; Heathcock, C. H. Top. Stereochem. 1992 19 338.
3. Haynes, R. K.; Starling, S. M.; Vonwiller, S. C. J. Org. Chem. 1995, 60, 4690.
4. However, the stereochemical outcome of the conjugate addition of a five-membered zinc chelate to a cyclopentenone is rationalized in terms of an endo-orientation of reactants: Takahashi, T.; Nakzawa, M.; Kanoh, M.; Yamamoto, K. Tetrahedron Lett. 1990, 31, 7349.
5. The proposals were set out in Honours proposal of A.C.R. at the University of Sydney.
6. Villieras, J.; Rambaud, M.; Graff, M. Tetrahedron Lett. 1985, 26, 53 Solladié, G.; Hutt, J.; Fréchou, C. Tetrahedron Lett. 1987, 28, 61.
7. Villieras, J.; Rambaud, M.; Graff, M. Tetrahedron Lett. 1985, 26, 53 Solladié, G.; Hutt, J.; Fréchou, C. Tetrahedron Lett. 1987, 28, 61.
8. This result implies that the lithiated ester has the (Z)-configuration in accord with the structure of lithiated allyl ethers; see: Yamamoto, Y.; Yatagi, H.; Maruyama, K. J. Org. Chem. 1980, 45, 195 and references therein.
9. Structures of 9, 10, and 12 were established by X-ray crystallography at the University of Sydney. Ratios of all isomers were established by measurement of reaction mixtures at 600 MHz
10. For a related case involving conjugate addition of silyl ketene acetals, see: Danishefsky, S. J.; Cabal, M. P.; Chow, K. J. Am. Chem. Soc. 1989, 111, 3456. Chow, K.; Danishefsky, S. J. J. Org. Chem. 1989, 54, 6016.
11. For a related case involving conjugate addition of silyl ketene acetals, see: Danishefsky, S. J.; Cabal, M. P.; Chow, K. J. Am. Chem. Soc. 1989, 111, 3456. Chow, K.; Danishefsky, S. J. J. Org. Chem. 1989, 54, 6016.
12. Eschler, B. M.; Haynes, R. K.; Ironside, M. D.; Kremmydas, S.; Ridley, D. D.; Hambley, T. W. J. Org. Chem. 1991, 66, 4760.
13. The use of the catalytic reagent to cleave tert-butyl ethers has been described recently: Franck, X.; Figadère, B.; Cavé, A. Tetrahedron Lett. 1995, 36, 711.
14. In the original strategy (ref 4), opening of the butenolide with its (Z)-configured double bond by alkoxide nucleophiles would be problematical. Conjugate addition of thiolate provides a saturated butanolide whose thiophenoxide-mediated opening is now favorable. Reversible elimination of thiolate provides the more stable (E)-unsaturated thioester, which is hydrolyzed on quenching to the acid.
15. Casy, G.; Gorins, G.; McCague, R.; Olivo, H. F.; Roberts, S. M. J. Chem. Soc., Chem. Commun. 1994, 1085; Carnell, A. J.; Casy, G.; Gorins, G.; Kompany-Saeid, A.; McCague, R.; Olivo, H. F.; Roberts, S. M.; Willetts, A. J. J. Chem. Soc., Perkin Trans. 1 1994, 3431.
16. Casy, G.; Gorins, G.; McCague, R.; Olivo, H. F.; Roberts, S. M. J. Chem. Soc., Chem. Commun. 1994, 1085; Carnell, A. J.; Casy, G.; Gorins, G.; Kompany-Saeid, A.; McCague, R.; Olivo, H. F.; Roberts, S. M.; Willetts, A. J. J. Chem. Soc., Perkin Trans. 1 1994, 3431.
17. Smith, A. B.; Rano, T. A.; Chida, N.; Sulikowski, G. A.; Wood, J. L. J. Am. Chem. Soc. 1992, 114, 8008.
18. 3, MeCN, reflux to give 21 (77%).
19. Evidently, under these conditions, acid-catalyzed isomerisation of the (Z)-alkene takes place.
20. D +90.0 (c 0.1, MeOH).
21. D +90.0 (c 0.1, MeOH).
22. For leading references, see: Boukouvalas, J. In Encyclopedia of Reagents for Organic Synthesis; Wiley: Chichester, 1995; Vol. 2, pp 820-823; Vol. 7, pp 5297-5300.
23. For leading references, see: Boukouvalas, J. In Encyclopedia of Reagents for Organic Synthesis; Wiley: Chichester, 1995; Vol. 2, pp 820-823; Vol. 7, pp 5297-5300.
24. Koeksal, Y.; Raddatz, P.; Winterfeldt, E. Angew. Chem., Int. Ed. Engl. 1980, 19, 472 and references cited therein.
25. The original intention was to add the vinyl cuprate corresponding to the protected (S)-heptenol side chain of brefeldin A to the enone 14 and then, after elimination of butoxide, treat the transposed enone (cf. 16) with the lithiated butenolide 2. While syntheses of brefeldin A employ conjugate additions of such organocuprates to cyclopentenones, we could not obtain workable yields of adducts. For relevant examples, see refs 4 and 12 and: Bernardes, V.; Kann, N.; Riera, A.; Moyano, A.; Pericas, M. A.; Greene, A. E. J. Org. Chem. 1995, 60, 6670. Kobayashi, Y.; Watatani, K.; Kikori, Y.; Mizojiri, R. Tetrahedron Lett. 1996, 37, 6125.
26. The original intention was to add the vinyl cuprate corresponding to the protected (S)-heptenol side chain of brefeldin A to the enone 14 and then, after elimination of butoxide, treat the transposed enone (cf. 16) with the lithiated butenolide 2. While syntheses of brefeldin A employ conjugate additions of such organocuprates to cyclopentenones, we could not obtain workable yields of adducts. For relevant examples, see refs 4 and 12 and: Bernardes, V.; Kann, N.; Riera, A.; Moyano, A.; Pericas, M. A.; Greene, A. E. J. Org. Chem. 1995, 60, 6670. Kobayashi, Y.; Watatani, K.; Kikori, Y.; Mizojiri, R. Tetrahedron Lett. 1996, 37, 6125.
27. For recent syntheses see refs 12 and 19 and: Miyaoka, H.; Kajiwara, M. J. Chem. Soc., Chem. Commun. 1994, 483. Tomioka, K.; Ishikawa, K.; Nakai, T. Synlett 1995, 901. Kim, D.; Lim, J. I. Tetrahedron Lett. 1995, 36, 5035.
28. For recent syntheses see refs 12 and 19 and: Miyaoka, H.; Kajiwara, M. J. Chem. Soc., Chem. Commun. 1994, 483. Tomioka, K.; Ishikawa, K.; Nakai, T. Synlett 1995, 901. Kim, D.; Lim, J. I. Tetrahedron Lett. 1995, 36, 5035.
29. For recent syntheses see refs 12 and 19 and: Miyaoka, H.; Kajiwara, M. J. Chem. Soc., Chem. Commun. 1994, 483. Tomioka, K.; Ishikawa, K.; Nakai, T. Synlett 1995, 901. Kim, D.; Lim, J. I. Tetrahedron Lett. 1995, 36, 5035.
30. For application of brefeldin A derivatives in induction of cell differentiation and apoptosis in cancer cell lines, see: Zhu, J.-W.; Hori, H.; Nojiri, H.; Tsukuda, T.; Taira, Z. Bioorganic Med. Chem. Lett. 1997, 7, 139.
31. The authors have deposited atomic coordinates for 9, 10, 12, and (R,S)-17 with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.