2006
DOI: 10.1016/j.tetlet.2005.11.143
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Reductive cyclisation of Morita–Baylis–Hillman adducts. A simple approach towards substituted hydrindanones and decalones

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Cited by 24 publications
(9 citation statements)
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“…Of those important C-C bond forming reactions, the Baylis-Hillman or Morita–Baylis–Hillman (MBH) reaction is a very useful and versatile one, which combines aldol and Michael reactions in a single step, providing organocatalyzed methylene--hydroxy carbonyl or -methylene--aminocarbonyl compounds. These compounds are very useful multifunctional building blocks in the synthesis of medicinally relevant pharmaceutical compounds [ 1 , 2 ] and natural products [ 3 ]. The interest in this atom-economical reaction has been growing, and good reviews regarding the development and progress using this reaction have been published [ 4 , 5 , 6 , 7 ].…”
Section: Introductionmentioning
confidence: 99%
“…Of those important C-C bond forming reactions, the Baylis-Hillman or Morita–Baylis–Hillman (MBH) reaction is a very useful and versatile one, which combines aldol and Michael reactions in a single step, providing organocatalyzed methylene--hydroxy carbonyl or -methylene--aminocarbonyl compounds. These compounds are very useful multifunctional building blocks in the synthesis of medicinally relevant pharmaceutical compounds [ 1 , 2 ] and natural products [ 3 ]. The interest in this atom-economical reaction has been growing, and good reviews regarding the development and progress using this reaction have been published [ 4 , 5 , 6 , 7 ].…”
Section: Introductionmentioning
confidence: 99%
“…The products afforded by the Baylis-Hillman reaction and their derivatives have served as an excellent source of several heterocyclic motifs. [1][2][3][4][5][6][7][8][9][10] In this context, our research group has successfully developed several simple, convenient, and high-yielding protocols for the synthesis of a variety of heterocyclic systems. [11][12][13][14][15][16][17][18][19] We have recently described syntheses of 3-methylene-2-pyrrolidinones and 3-(1-alkoxycarbonylvinyl)-1H-indole-2-carboxylates.…”
Section: Introductionmentioning
confidence: 99%
“…Alkaline treatment of 23 resulted in the hydrolysis of the acetyl group, removal of the resulting formyl group, and epimerization at the ring juncture to trans, which was followed by regioselective hydrolysis of the exposed ester to provide hydroxy-acid 24. Addition of 3-furyllithium to aldehyde 27 furnished racemic teucvin C (28) and 12-epi-teucvin C (29).…”
mentioning
confidence: 99%
“…Marko et al reported the synthesis of decalone 155 bearing the requisite functional groups for clerodane natural product syntheses by intramolecular reductive alkylation of the Morita-Baylis-Hillman (M-B-H) adduct 153 between aldehyde 152 and 2-cyclohexen-1-one (Scheme 16). 29 The adduct 153 was obtained in good yield employing (n-Bu) 3 P and BINOL, the reaction conditions developed by Ikegami et Scheme 10. Total synthesis of (±)−6-acetoxy-2-oxokolavenool (97).…”
mentioning
confidence: 99%
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