Efficient synthesis of akolactone A via Pd-catalyzed carbonylation

Bioscience, Biotechnology and Biochemistry

Volumn 67, Issue 12, 2003, Pages 2658-2660

  Makabe, Hidefumi ^a   Okajima, Motonori ^a   Konno, Hiroyuki ^b   Kamo, Tsunashi ^a   Hirota, Mitsuru ^a  

^a SHINSHU UNIVERSITY   (Japan)

^b UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

, unsaturated lactone; Pd catalyzed carbonylation

Indexed keywords

AKOLACTONE A; ANTINEOPLASTIC AGENT; DRUG DERIVATIVE; GAMMA BUTYROLACTONE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; SYNTHESIS;

4-BUTYROLACTONE; ANTINEOPLASTIC AGENTS; CATALYSIS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 4544361917     PISSN: 09168451     EISSN: None     Source Type: Journal    
DOI: 10.1271/bbb.67.2658     Document Type: Article

References (7)

1. Chen, I.-S., Lai-Yaun, I.-L., Duh, C.-Y., and Tsai, I.-L., Cytotoxic butanolides from Litsea akoensis. Phytochemistry, 49, 745-750 (1998).
2. Smith, W. N., and Beumel, Jr. O. F., Preparation of alkynes and dialkynes by reaction of monohalo- and dihaloalkanes with lithium acetylide- ethylenediamine complex. Synthesis, 441-442 (1974).
3. Sonogashira, K., Tohda, Y., and Hagihara, N., Convenient synthesis of acetylenes. Catalytic substitutions of acetylenic hydrogen with bromo alkenes, iodo arenes, and bromopyridines. Tetrahedron Lett., 4467-4470 (1975).
4. Alami, M., Ferri, F., and Linstrumelle, G., An efficient palladium-catalyzed reaction of vinyl and aryl halides or triflates with terminal alkynes. Tetrahedron Lett., 34, 6403-6406 (1993).
5. Schoenberg, A., Bartoletti, I., and Heck, R. F., Palladium-catalyzed carboalkoxylation of aryl, benzyl, and vinylic halides. J. Org. Chem., 39, 3318-3326 (1974).
6. Vittorio, F., and Magnus, E., Intramolecular cyclization processes via palladium-catalyzed carbonylative lactonization and lactamization. In "Handbook of Organopalladium Chemistry", ed. Negishi, E., Wiley-Interscience, New York, pp. 2351-2375 (2002).
7. Hoye, T. R., and Zhixiong, Y., Highly efficient synthesis of the potent antitumor annonaceous acetogenin (+)-parviflorin. J. Am. Chem. Soc., 118, 1801-1802 (1996).