Enantiodivergent chemoenzymatic synthesis of (S)- and (R)-(Z)-9-Dodecyl-4, 5,8,9-tetrahydro-3H-oxonin-2-one as analogues of topsentolides

Letters in Organic Chemistry

Volumn 9, Issue 3, 2012, Pages 169-174

  Wetzel, Isolde ^a   Krauss, Jürgen ^a   Bracher, Franz ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

Cytotoxic activity; Grubbs catalyst; Kinetic enzymatic resolution; Lipase; Ring closing metathesis; Topsentolides

Indexed keywords

EID: 84860577092     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017812800167466     Document Type: Article

References (36)

1. Gradillas A., Prez-Castells J. Macrocyclization by ring-closing metathesis in the total synthesis of natural products: Reaction conditions and limitations. Angew. Chem. Int. Ed. 2006 45 6086.
2. Parently A., Moreau X., Campagne J.-M. Macrolactonizations in the total synthesis of natural products. Chem. Rev. 2006 106 911.
3. Kumara Swamy K. C., Bhuvan Kumar N. N., Balaraman E., Pavan Kumar K. V. P. Mitsunobu and related reactions: Advances and applications. Chem. Rev. 2009 109 2551.
4. Fürstner A., Kindler N. Macrocycle formation by ring- closingmetathesis. An efficient synthesis of enantiomerically pure (R)-(+)-lasiodiplodin. Tetrahedron Lett. 1996 37 7005.
5. Fürstner A. Olefin metathesis and beyond. Angew. Chem. Int. Ed. 2000 39 3012.
6. Amigoni S. J., Toupet L. J., Le Floc'h Y. J. Enantioselective total synthesis of the (-)-(6R,11R,14S)-isomer of colletallol. J. Org. Chem. 1997 62 6374
7. Krauss J., Unterreitmeier D., Neudert C., Bracher F. Short and efficient approach towards macrocyclic lactones based on a Sonogashira reaction. Arch. Pharm. Pharm. Med. Chem. 2005 338 605.
8. Gerlach H., 2-(Trimethylsilyl)äthylester als Carboxylschutzgruppe; Anwendung bei der Synthese des (-)-(S)-Curvularins. Helv. Chim. Acta 1977 60 3039.
9. Bracher F., Schulte B. A chemoenzymatic synthesis of the macrocyclic lactone (S)-curvularin. Nat. Prod. Lett. 1995 7 65.
10. Ferraz H. M. C., Bombonato F. I., Sano M. K., Longo Jr., L. S. Natural occurrence biological activities and synthesis of eight- nine- and eleven-membered ring lactones. Quim. Nova 2008 31 885.
11. Shiina; I. Total synthesis of natural 8-and 9-membered lactones: Recent advancements in medium-sized ring formation. Chem. Rev. 2007 107 239.
12. Luo X., Li F., Hong J., Lee C.-O., Sim C. J., Im K. S., Jung J. H. Cytotoxic oxylipins from a marine sponge Topsentia sp. J. Nat. Prod. 2006 69 567.
13. White J. D., Yang J. Strategies for the synthesis of the cyclopropyl-substituted lactone family of oxylipins. Synlett 2009 1713.
14. Kobayashi M., Ishigami K., Watanabe H. Determination of the absolute configuration of marine oxylipin topsentolide A1 by the synthesis of the enantiomer of the natural product. Tetrahedron Lett. 2010 51 2762.
15. Inanaga J., Hirata K., Saeki H., Katsuki T., Yamaguchi M. A Rapid esterification by means of mixed anhydride and its application to large-ring lactonization. Bull. Chem. Soc. Jpn. 1979 52 1989.
16. Baltrusch A. W., Bracher F. Enantioselective synthesis of 6-norfluvirucinin B1. Synlett 2002 1724.
17. Bracher F., Schulte B. An enantiodivergent synthesis of both enantiomers of the macrocyclic lactone lasiodiplodin. J. Chem. Soc., Perkin Trans. 1 1996 2619.
18. Bracher F., Schulte B. An enantiodivergent synthesis of both enantiomers of the macrocyclic lactone curvularin. Liebigs Ann./Recueil 1997 1979.
19. Bracher F., Krauss J. Total synthesis of zearalanone. Monatsh. Chem. 2001 132 805.
20. Bracher F., Krauss J. The total synthesis of both enantiomers of the macrocyclic lactone zearalane. Eur. J. Org. Chem. 2001 4701.
21. Bracher F., Schulte B. Total synthesis of both enantiomers of the macrocyclic lactone citreofuran. Nat. Prod. Res. 2003 17 293.
22. Krauss J., Bracher F., Unterreitmeier D. New approach towards cytotoxic furyl macrolactones by ring closing metathesis. Arch. Pharm. Pharm. Med. Chem. 2006 339 629.
23. Schmidt C., Messmer R., Bracher F., Krauß J. New approach towards furan containing macrolactones. Turk. J. Chem. 2007 31 251.
24. Krauss J., Koebler D., Miller V., Bracher F. Synthesis by ring closing metathesis and cytotoxic evaluation of novel thienyl macrolactones. Sci. Pharm. in press (doi:10.3797/scipharm.1109-09).
25. Bracher F; Papke T. A biocatalytic approach to nonracemic 2-methyl-3-(2-thiophene)-1-propanols as chiral building blocks for the synthesis of pyridine alkaloids. Tetrahedron Asymm. 1994 5 1653.
26. Bracher F., Litz T. An efficient chemoenzymatic route to the antidepressants (R)-fluoxetine and (R)-tomoxetine. Bioorg. Med. Chem. 1996 4 877.
27. Kazlauskas R. J., Weissfloch A. N. E., Rappaport A. T., Cuccia L. A. A rule to predict which enantiomer of a secondary alcohol reacts faster in reactions catalyzed by cholesterol esterase lipase from Pseudomonas cepacia and lipase from Candida rugosa. J. Org. Chem. 1991 56 2656.
28. Fujii M., Fukumura M., Hori Y., Hirai Y., Akita H., Nakamura K., Toriizuka K., Ida Y. Chemoenzymatic synthesis of optically active -alkyl-butenolides. Tetrahedron Asymm. 2006 17 2292.
29. Mitsunobu O., The use of diethyl azodicarboxylate and triphenylphosphine in synthesis and transformation of natural products. Synthesis 1981 1.
30. Baba Y., Saha G., Nakao S., Iwata C., Tanaka T., Ibuka T., Ohishi H., Takemoto Y. Asymmetric total synthesis of halicholactone. J. Org. Chem. 2001 66 81.
31. Takahashi T., Watanabe H., Kitahara T. Total synthesis of (-)-halicholactone. Heterocycles 2002 58 99.
32. Zhu C.-Y., Cao X.-Y., Zhu B.-H., Deng C., Sun X.-L., Wang B.-Q., Shen Q., Tang Y. Application of asymmetric ylide cyclopropanation in the total synthesis of halicholactone. Chem. Eur. J. 2009 15 11465.
33. Ramirez-Fernandez J., Collado I. G., Hernandez-Galan R. Effect of substituts on the ring-closing metathesis reaction in the synthesis of functionalized nonanolactones. Synlett 2008 339.
34. Sreedhar E., Venkanna A., Chandramouli N., Babu K. S., Rao J., M. The first total synthesis of topsentolide B3. Eur. J. Org. Chem. 2011 1078.
35. Fürstner A., Thiel O. R., Ackermann L. Exploiting the reversibility of olefin metathesis. Syntheses of macrocyclic trisubstituted alkenes and (R,R)-(-)-pyrenophorin. Org. Lett. 2001 3 449.
36. Mosmann T. J., Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxic assays. J. Immunol. Methods 1983 65 55.