A Novel Synthesis of 1-Acetyl-4-Isopropenyl-1-Cyclopentene by Chemoselective Cyclization of 4-Methyl-3-(Oxobutyl)-4-Pentenal: An Important Intermediate for Natural Product Synthesis

Journal of the Brazilian Chemical Society

Volumn 10, Issue 2, 1999, Pages 112-116

  Castro, Fernando De Lima ^a   Kover, Renata Xavier ^a   Kover, Warner Bruce ^a   Jones Jr , Joel ^a  

^a FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

Author keywords

Chemoselective cyclization; Epoxide ring opening; KIO4 oxidation; Terpenoid chirons

Indexed keywords

EID: 0347708734     PISSN: 01035053     EISSN: None     Source Type: Journal    
DOI: 10.1590/S0103-50531999000200007     Document Type: Article

References (24)

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6. For leading examples on the use of terpenes in chiral synthesis, see: (a) Money, T. Nat.Prod.Rep. 1985, 2, 253. (b) Money, T. Studies in Natural Products Chemistry. Stereoselective Synthesis; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam 1989, vol. IV, Part C, p 625. (c) Thomas, F.; Bessiere, Y. Nat. Prod. Rep. 1989, 6, 291. (d) Corey, E.J.; Cheng, X.M. The Logic of Chemical Synthesis; John Wiley & Sons: New York, 1989. (e) Ho, T.-L. Enantioselective Synthesis: Natural Products from Chiral Terpenes; John Wiley&Sons, New York, 1992.
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24. Interestingly, ketone 4 was calculated to be 0.5 kcal less stable than the aldehyde 5 using MM2 (Macro-Model) in a Monte Carlo simulation.