An enantioselective Mukaiyama aldol reaction as the key step towards the tetrahydropyran core of psymberin via a γ-butyrolactone intermediate

Synlett

Volumn 23, Issue 11, 2012, Pages 1625-1628

  Bielitza, Max ^a   Pietruszka, Jörg ^a  

^a HEINRICH HEINE UNIVERSITY   (Germany)

Author keywords

aldol reaction; antitumor agent; asymmetric catalysis; enantioselectivity; lactone

Indexed keywords

BUTYROLACTONE; GAMMA LACTONE DERIVATIVE; PEDERIN; PSYMBERIN; PYRAN DERIVATIVE; TETRAHYDROPYRAN; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; LACTONIZATION; MUKAIYAMA REACTION; REDUCTION; STEREOCHEMISTRY;

EID: 84862169926     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0031-1290379     Document Type: Article

References (28)

1. Cichewicz RH, Valeriote FA, Crews P. Org. Lett.: 2004; 6 1951
2. Pettit GR, Xu JP, Chapuis JC, Pettit RK, Tackett LP, Doubek DL, Hooper JN. A, Schmidt JM. J. Med. Chem.: 2004; 47 1149
3. Jiang X, Garcia-Fortanet J, De Brabander JK. J. Am. Chem. Soc.: 2005; 127 11254
4. Huang X, Shao N, Palani A, Aslanian R, Buevich A. Org. Lett.: 2007; 9 2597
5. Smith AB III, Jurica JA, Walsh SP. Org. Lett.: 2008; 10 5625
6. Crimmins MT, Stevens JM, Schaaf GM. Org. Lett.: 2009; 11 3990
7. Watanabe T, Imaizumi T, Chinen T, Nagumo Y, Shibuya M, Usui T, Kanoh N, Iwabuchi Y. Org. Lett.: 2011; 12 1040
8. Wan S, Wu F, Rech JC, Green ME, Balachandran R, Horne WS, Day BW, Floreancig PE. J. Am. Chem. Soc.: 2011; 133 16668
9. Byeon SR, Park H, Kim H, Hong J. Org. Lett.: 2011; 13 5816
10. Kiren S, Williams LJ. Org. Lett.: 2005; 7 2905
11. Green ME, Rech JC, Floreancig PE. Org. Lett.: 2005; 7 4117
12. Rech JC, Floreancig PE. Org. Lett.: 2005; 7 5175
13. Huang X, Shao N, Palani A, Aslanian R, Buevich A, Seidel-Dugan C, Huryk R. Tetrahedron Lett.: 2008; 49 3592
14. Lachance H, Marion O, Hall DG. Tetrahedron Lett.: 2008; 49 6061
15. Brown LE, Landaverry YR, Davies JR, Milinkevich KA, Ast S, Carlson JS, Oliver AG, Konopelski JP. J. Org. Chem.: 2009; 74 5405
16. Henßen B, Kasparyan E, Marten G, Pietruszka J. Heterocycles: 2007; 245
17. Pietruszka J, Simon RC. Eur. J. Org. Chem.: 2009; 3628
18. Piel J, Butzke D, Fusetani N, Hui D, Platzer M, Wen G, Matsunaga S. J. Nat. Prod.: 2005; 68 472
19. Fisch KM, Gurgui C, Heycke N, van der Sar SA, Anderson SA, Webb VL, Taudien S, Platzer M, Rubio BK, Robinson SJ, Crews P, Piel J. Nat. Chem. Biol.: 2009; 5 494
20. Mukaiyama T, Narasaka K, Banno K. Chem. Lett.: 1973; 1011
21. Mukaiyama T, Banno K, Narasaka K. J. Am. Chem. Soc.: 1974; 96 7503
22. Lovchik MA, Goeke A, Fráter G. J. Org. Chem.: 2007; 72 2427
23. Lu Y, Woo SK, Krische MJ. J. Am. Chem. Soc.: 2011; 133 13876
24. Molander GA. In Science of Synthesis - Stereoselective Synthesis. Vol. 2 Liu L, Wang D, Li C.-J. Thieme Stuttgart: 2011; 585
25. Mahrwald R. Chem. Rev.: 1999; 99 1095
26. Nelson SG. Tetrahedron: Asymmetry: 1998; 9 357
27. Evans DA, Burgey CS, Kozlowski MC, Tregay SW. J. Am. Chem. Soc.: 1999; 121 686
28. Evans DA, MacMillan DW. C, Campos KR. J. Am. Chem. Soc.: 1997; 119 10859