A highly diastereoselective, tandem Mukaiyama aldol-lactonization route to β-lactones: Application to a concise synthesis of the potent pancreatic lipase inhibitor, (-)-panclicin D

Journal of Organic Chemistry

Volumn 62, Issue 1, 1997, Pages 4-5

  Yang, Hong Woon ^a   Romo, Daniel ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ENZYME INHIBITOR; LACTONE DERIVATIVE; PANCLICIN D; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031021953     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9619488     Document Type: Article

References (25)

1. (a) For a recent review of β-lactone chemistry, see: Pommier A.; Pons, J.-M. Synthesis 1993, 441-449. For recent reviews of β-lactone-containing natural products, see:
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3. (c) Pommier, A.; Pons, J. M. Synthesis 1995, 729-744.
4. (d) For a lead reference to polymers derived from β-lactones, see: Jedlinski, Z.; Kurcok, P.; Kowalczuk, M.; Matuszowicz, A.; Dubois, P.; Jerome, R.; Kricheldorf, H. R. Macromolecules 1995, 28, 7276-7280.
5. Reetz, M. T.; Schmitz, A.; Holdgrun, X. Tetrahedron Lett. 1989, 30, 5421-5424.
6. (a) Hirai, K.; Homma, H.; Mikoshiba, I. Heterocycles 1994, 38 281-282
7. (b) For related work involving the one-step synthesis of β-lactams, see: Annunziata, R.; Cinquini, M.; Cozzi, F.; Molteni, V.; Schupp, O. Tetrahedron 1996, 52, 2573-2582.
8. (a) Danheiser, R. L.; Nowick, J. S. J. Org. Chem 1991 56, 1176-1185
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10. Wedler, C.; Kleiner, K.; Kunath, A.; Schick, H. Liebigs. Ann. 1996, 881-885 and references cited.
11. The ketene thioacetals 2b (∼20:1 Z (O):E (O)) and 2c are readily prepared from the corresponding acids in two steps by standard acylation and silylation, see: Hirai, K.; Iwano, Y.; Mikoshiba, I.; Koyama, H.; Nishi, T. Heterocycles 1994, 38, 277-280 and ref 3b.
12. For a recent report of the use of ketene thiopyridylacetals in aldol reactions, see: Sun, K.-H.; Choo, D.-J. Tetrahedron Lett. 1995, 36, 6109-6112.
13. Isolation and biological activity: (a) Yoshinari, K.; Aoki, N.; Ohtsuka, T.; Nakayama, N.; Itezono, Y.; Mutoh, M.; Watanabe J.; Yokose, K. J. Antibiot. 1994, 47, 1376-1384. Structure determination: (b) Mutoh, M.; Nakada, N.; Matsukuma S.; Ohshima S.; Yoshinari, K.; Watanabe, J.; Arisawa, M. J. Antibiot. 1994, 47, 1369-1375.
14. Isolation and biological activity: (a) Yoshinari, K.; Aoki, N.; Ohtsuka, T.; Nakayama, N.; Itezono, Y.; Mutoh, M.; Watanabe J.; Yokose, K. J. Antibiot. 1994, 47, 1376-1384. Structure determination: (b) Mutoh, M.; Nakada, N.; Matsukuma S.; Ohshima S.; Yoshinari, K.; Watanabe, J.; Arisawa, M. J. Antibiot. 1994, 47, 1369-1375.
15. Zhi J.; Melia, A. T.; Guerciolini, R.; Chung, J.; Kinberg, J.; Hauptman, J. B.; Patel, I. H. Clin. Pharm. Ther. 1994, 56, 82.
16. A general procedure for the tandem Mukaiyama aldol-lactonization can be found in the supporting information.
17. Kim, S.; Lee, J. I. J. Org. Chem. 1984, 49, 712-1716.
18. Mulzer, J.; Zippel, M.; Bruntrup, G.; Segner, J.; Finke, J. Liebigs Ann. Chem. 1980, 1108.
19. Geennari, C.; Beretta, M. G.; Bernardi, A.; Moro, G.; Scolastico, C.; Todeschini, R. Tetrahedron 1986, 42, 893-909.
20. The X-ray data of β-lactone 3h has been deposited with the Cambridge Crystallographic Data Centre. The crdinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
21. A related process has been previously observed in Al-catalyzed [2 + 2] cycloadditions of ketenes and both aromatic and α,β-unsaturated aldehydes: Conception, A. B.; Maruoka, K.; Yamamoto, H. Tetrahedron 1995, 51, 4011-4020.
22. 1H NMR, cf. Mead, K. T.; Park, M. J. Org. Chem. 1992, 57, 2511-2514). The relative stereochemistry has not been determined at this time but is based on the expected, initially formed trans-β-lactone undergoing an inversion process during intramolecular cyclization of the pendant ether (unpublished results of M. Scott Champ). Chemical Equation presented it.
23. Racherla, U. S.; Brown, H. C. J. Org. Chem. 1991, 56, 401-404.
24. 2Si β-cylodextrin column: Shitangkoon, A.; Vigh, G. J. Chromatogr. A 1996, 31-42.
25. This ketene acetal was prepared in three steps from lauric acid. See supporting information for experimental details.