36866-68-9Relevant academic research and scientific papers
Formal [4 + 1]- and [5 + 1]-annulation by an SN2-conjugate addition sequence: Stereoselective synthesis of highly substituted carbocycles
Tong, Benny Meng Kiat,Chen, Hui,Chong, Sin Yee,Heng, Yi Li,Chiba, Shunsuke
supporting information; experimental part, p. 2826 - 2829 (2012/08/07)
K2CO3-mediated reactions of 6-bromo-2-hexenoates and 7-bromo-2-heptenoate with active methylene compounds deliver highly substituted cyclopentane and cyclohexane derivatives, respectively via a sequence of S N2-conjugate a
Exploration of the interrupted Fischer indolization reaction
Schammel, Alex W.,Boal, Ben W.,Zu, Liansuo,Mesganaw, Tehetena,Garg, Neil K.
supporting information; experimental part, p. 4687 - 4695 (2010/08/06)
A convergent method to access the fused indoline ring system present in a multitude of bioactive molecules has been developed. The strategy involves the condensation of hydrazines with latent aldehydes to ultimately deliver indoline-containing products by way of an interrupted Fischer indolization sequence. The method is convergent, mild, operationally simple, broad in scope, and can be used to access enantioenriched products. In addition, our approach is amenable to the synthesis of furoindoline and pyrrolidinoindoline natural products as demonstrated by the concise formal total syntheses of physovenine and debromoflustramine B. The strategy will likely enable the synthesis of more complex targets such as the communesin alkaloids.
An interrupted fischer indolization approach toward fused indoline-containing natural products
Boal, Ben W.,Schammel, Alex W.,Garg, Neil K.
supporting information; experimental part, p. 3458 - 3461 (2009/12/07)
An efficient method to access the fused indoline ring system present in a multitude of bioactive molecules has been developed. The strategy involves the condensation of hydrazines with latent aldehydes to ultimately deliver indoline-containing products by way of an interrupted Fischer indolization sequence. Our studies show that the approach will likely be amenable to the synthesis of complex targets, such as the communesin natural products.
Synthesis of 4,4′-disubstituted azepines via ring-closing metathesis reaction and asymmetric arylation of lactones
Delhaye, Laurent,Merschaert, Alain,Diker, Khalid,Houpis, Ioannis N.
, p. 1437 - 1442 (2007/10/03)
The syntheses of the title compounds were accomplished via an original sequence of reactions including the ring-closing metathesis of ω-dienes by using the second-generation Grubbs' catalyst. The chiral diene precursors are available in racemic or optical
Stereoselective Substitution at Phenyl-Substituted γ-Lactols with Organometallic Compounds
Schmitt, Andreas,Reissig, Hans-Ulrich
, p. 871 - 876 (2007/10/02)
A variety of monosubstituted γ-lactols 4-6 were prepared in good yields by DIBAL reduction of the corresponding γ-lactones 1-3.The monophenyl-substituted lactols 4b-6b were transformed into disubstituted tetrahydrofuran derivatives by replacement of the hydroxyl group by the alkyl residue of organometallic compounds used as nucleophiles.The diastereoselectivity of the substitution was found to depend strongly on the substitution pattern of the γ-lactols.For the reaction of the 3- and 4-substituted derivatives 4b and 5b, respectively, good to excellent trans selectivity was observed, while the 5-substituted derivative reacted without any diastereoselectivity.These results were interpreted by means of the Felkin-Anh model. - Keywords: γ-Lactone / Reduction / γ-Lactol / Lewis acid / Tetrahydrofurans
