The second generation synthesis of (+)-pseudodeflectusin

Tetrahedron Letters

Volumn 52, Issue 5, 2011, Pages 626-629

  Sato, Yuna ^a   Kuramochi, Kouji ^a   Suzuki, Takahiro ^a   Nakazaki, Atsuo ^a   Kobayashi, Susumu ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

(+) Pseudodeflectusin; Antitumor activity; Cascade reaction; Formal total synthesis; Regioselective Diels Alder reaction

Indexed keywords

ALKYNE; ANTINEOPLASTIC AGENT; HYDROXYPYRONE; PSEUDODEFLECTUSIN; SODIUM HYDROXIDE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; DECARBOXYLATION; DIELS ALDER REACTION; DRUG SYNTHESIS; ISOMER; LACTONIZATION; NONHUMAN;

ALNUS;

EID: 78651104959     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.11.153     Document Type: Article

References (15)

1. A. Ogawa, C. Murakami, S. Kamisuki, I. Kuriyama, H. Yoshida, F. Sugawara, and Y. Mizushima Bioorg. Med. Chem. Lett. 14 2004 3539 3543
2. F. Saito, K. Kuramochi, A. Nakazaki, Y. Mizushina, F. Sugawara, and S. Kobayashi Eur. J. Org. Chem. 2006 4796 4799
3. K. Kuramochi, F. Saito, A. Nakazaki, T. Takeuchi, K. Tsubaki, F. Sugawara, and S. Kobayashi Biosci. Biotechnol. Biochem. 74 2010 1635 1640
4. M. Tobe, T. Tashiro, M. Sasaki, and H. Takikawa Tetrahedron 63 2007 9333 9337
5. Bromolactone 5 was prepared by bromination/elimination sequence of the corresponding lactone. See Ref. 6
6. S. Vijgen, K. Nauwelaerts, J. Wang, A.V. Aerschot, I. Lagoja, and P. Herdewijn J. Org. Chem. 70 2005 4591 4597
7. T. Komiyama, Y. Yakaguchi, A.T. Gubaidullin, V.A. Mamedov, I.A. Litvinov, and S. Tsuboi Tetrahedron 61 2005 2541 2547
8. N.P.H. Tan, and C.D. Donner Tetrahedron 65 2009 4007 4012
9. +] 311; found 311.
10. K. Itoh, S. Iwata, and S. Kishimoto Heterocycles 68 2006 395 400
11. H. Okamura, T. Iwagawa, and M. Nakatani J. Synth. Org. Chem. Jpn. 57 1999 84 91
12. H. Okamura, Y. Nakamura, T. Iwagawa, and M. Nakatani Chem. Lett. 1996 193 194
13. +] 278.9627; found 278.9617.
14. A. Krasovskiy, and P. Knochel Angew. Chem., Int. Ed. 43 2004 3333 3336
15. M. Mori, N. Kaneta, N. Isono, and M. Shibasaki J. Organomet. Chem. 455 1993 255 260