- Total synthesis of (±)-β-microbiotene, (±)-microbiotol, (±)-cyclocuparanol and (±)-β-cuparenones
-
Total synthesis of (±)-β-microbiotene, (±)-microbiotol, (±)-cyclocuparanol and their epimers along with (±)-β- cuparenone has been described. A combination of orthoester Claisen rearrangement, an acid catalysed rearrangement of a diazoketone for the gener
- Srikrishna,Ramachary
-
p. 805 - 817
(2008/09/18)
-
- A short and efficient synthesis of (±)-β-cuparenone
-
A Wittig olefination-Claisen rearrangement strategy has been applied to achieve one of the shortest and efficient synthesis of (±)-β-cuparenone.
- Kulkarni, Mukund G.,Davawala, Saryu I.,Shinde, Mahadev P.,Dhondge, Attrimuni P.,Borhade, Ajit S.,Chavhan, Sanjay W.,Gaikwad, Dnyaneshwar D.
-
p. 3027 - 3029
(2007/10/03)
-
- Nickel-catalysed conjugate addition to trimethylaluminum to sterically hindered α,β-unsaturated ketones
-
Nickel acetylacetonate is an efficient catalyst for the 1,4-addition of trimethylaluminum to α,β-unsaturated ketones. The reaction is strongly solvent dependent and gives best results in tetrahydrofuran or ethyl acetate. The reaction is especially useful for the nucleophilic 1,4-methyl transfer to sterically hindered enones. A β-cuparenone synthesis via conjugate methyl group addition to an enone precursor is described.
- Flemming,Kabbara,Nickish,Neh,Westermann
-
p. 317 - 320
(2007/10/02)
-
- Total Synthesis of (+/-)-Cyclolaurene, (+/-)-Epicyclolaurene and (+/-)-β-Cuparenone
-
The first total synthesis of (+/-)-cyclolaurene (1) and (+/-)-epicyclolaurene (5), and a new route to (+/-)-β-cuparenone (4) are reported.Thus, orthoester Claisen rearrangement of the cinnamyl alcohol 8 furnished the ene-ester 10.Anhydrous CuSO4 catalysed
- Srikrishna, Adusumilli,Krishnan, Kathiresan
-
p. 3429 - 3436
(2007/10/02)
-
- ENANTIOCONTROLLED SYNTHESES OF THE CUPARENE SESQUITERPENES, (-)-HERBERTENE, (+)-β-CUPARENONE, (-)-DEBROMOAPLYSIN, AND (-)-APLYSIN
-
Enantiocontrolled syntheses of the Cuparene sesquiterpenes, (-)-herbertene, (+)-cuparenone, (-)-debromoaplysin, and (-)-aplysin, have been achieved starting from the optically active tricyclic dienone by employing a Fischer indolization reaction under non-acidic conditions as the key step.
- Takano, Seiichi,Moriya, Minoru,Ogasawara, Kunio
-
p. 329 - 332
(2007/10/02)
-
- SYNTHESIS AND UTILIZATION OF OPTICALLY ACTIVE 2-SUBSTITUTED 4-(TRIMETHYLSILYL)CYCLOPENTANONES: SYNTHESIS OF (-)-MASSOIALACTONE AND (+)-β-CUPARENONE
-
Ring contraction by BF3*Et2O catalyzed epoxide rearrangement of 3-substituted 5-trimethylsilyl-2,3-epoxycyclohexanones gave the corresponding 2-substituted 4-(trimethylsilyl)cyclopentanones diastereoselectively.Synthesis of (-)-massoialactone and (+)-β-cuparenone utilizing the above transformation is also described.
- Asaoka, Morio,Hayashibe, Satoshi,Sonoda, Syuzo,Takei, Hisashi
-
p. 4761 - 4764
(2007/10/02)
-
- TOTAL SYNTHESIS OF (R)-(-)-β-CUPARENONE
-
(R)-(-)-β-Cuparenone has been synthesized from (S)-(+)-acid-2 obtained via resolution of the racemic acid.Two of the noteworthy steps are (a) repeated methylation of ester (+)-8 with LDA/MeI to furnish (+)-10 and (b) the reaction of 12, having two neopent
- Gharpure, Milind M.,Rao, A. S.
-
p. 679 - 688
(2007/10/02)
-
- Ultrasound in Organic Synthesis. 7. Preparation of Organozinc Reagents and Their Nickel-Catalyzed Reactions with α,β-Unsaturated Carbonyl Compounds
-
Diorganozinc compounds can be prepared with great ease and efficiency in a one-pot process, by sonication of lithium, an organic halide, and a zinc halide in THF or toluene mixtures.The reagents thus obtained give rise to clean and selective conjugate additions to α,β-unsaturated aldehydes and ketones in the presence of catalytic amounts of nickel acetylacetonate.
- Petrier, Christian,Barbosa, Jayne C. de Souza,Dupuy, Claude,Luche, Jean-Louis
-
p. 5761 - 5765
(2007/10/02)
-
- EFFICIENT REGIOSELECTIVE SYNTHESES OF α AND β CUPARENONES. A NEW APPROACH FOR THE CONSTRUCTION OF THE CYCLOPENTANE RING
-
This paper discloses the regioselective synthesis of the cyclopentane ring from a carbonyl compound via two ring expension reactions.
- Halazy, S.,Zutterman, F.,Kries, A.
-
p. 4385 - 4388
(2007/10/02)
-
- TOTAL SYNTHESIS OF THE SESQUITERPENE (+/-)β-CUPARENONE: USE OF THREE-CARBON ANNULATION IN SYNTHESIS
-
A total synthesis of β-cuparenone, which highlights the advantages and disadvantages of the three-carbon annulation process, is described.
- Jung, Michael E.,Radcliffe, C. David
-
p. 4397 - 4400
(2007/10/02)
-