Showing papers by "Tomas Hudlicky published in 2008"
TL;DR: Solid-state silica-gel-catalyzed opening of aziridine 6 provided phenanthrene 7, whose oxidative cleavage, recyclization, and further elaboration furnished the C-1 aldehyde and carboxylic acid derivatives of 7-deoxypancratistatin for potential analogue synthesis.
42 citations
TL;DR: Hydrocodone was converted to various N-acyl derivatives via a one-pot N-demethylation/N-acylation protocol catalyzed by palladium(II), and a plausible mechanism is suggested.
Abstract: Hydrocodone was converted to various N-acyl derivatives via a one-pot N-demethylation/N-acylation protocol catalyzed by palladium(II). The procedure has also been successfully applied to several N-methyltropane alkaloids. A plausible mechanism is suggested.
42 citations
TL;DR: In this article, a total synthesis of (−)-balanol was accomplished from bromobenzene in 13 steps via the bis-benzyl derivative 3, whose optical rotation data have been provided.
20 citations
TL;DR: An efficient formal synthesis of a (-)-balanol intermediate from cyclohexadiene oxide was accomplished in eight steps with an asymmetric version of the Burgess reagent allowing for an enantiodivergent approach to both enantiomers of balanol from a racemic starting material.
Abstract: An efficient formal synthesis of a (−)-balanol intermediate (25a) from cyclohexadiene oxide was accomplished in eight steps. An asymmetric version of the Burgess reagent allows for an enantiodivergent approach to both enantiomers of balanol from a racemic starting material.
18 citations
Patent•
30 Jun 2008TL;DR: In this paper, the conversion of the thebaine to a morphine derivative, such as hydrocodone, is described, and a one-pot procedure for the conversion comprises treating the baine with an acid in the presence of a metal catalyst.
Abstract: The present invention provides methods for the conversion of the thebaine to a morphine derivative, such as hydrocodone. Novel ketal intermediates fo the conversion are provided. A one-pot procedure for the conversion comprises treating thebaine with an acid in the presence of a metal catalyst.
15 citations
Patent•
30 Jun 2008TL;DR: In this paper, a one-pot method for N-demethylation and/or Nacylation of a tertiary N-methylated heterocycle such as morphine alkaloids or tropane alkaloid was proposed.
Abstract: The present invention relates to a one-pot method for N-demethylation and/or N-acylation of a tertiary N-methylated heterocycle such as morphine alkaloids or tropane alkaloids The method, exemplified by Scheme 1, comprises reacting said tertiary N-methylated heterocycle with an acylatmg agent in the presence of a Pd metal catalyst.
11 citations
Patent•
30 Jun 2008TL;DR: In this paper, a method for N-demethylation of a tertiary N-methylated heterocycle, particularly a morphine or tropane alkaloids or derivatives thereof, was presented.
Abstract: The present invention relates to a method for N-demethylation of a tertiary N-methylated heterocycle, particularly a morphine or tropane alkaloids or derivatives thereof. The method, comprises reacting said tertiary N-methylated heterocycle with a metal catalyst, for example Pd(OAc)2 or Cu(OAc)2 in the presence of an oxidizing agent such as oxygen or ammonium persulfate.
8 citations
TL;DR: In this paper, 2-methylpiperidine and 2-cyclohexyl piperidine were converted to their respective β-keto amides by treatment with diketene.
Abstract: 2-Methylpiperidine and 2-cyclohexylpiperidine were converted to their respective β-keto amides by treatment with diketene. Several strains of yeast were used to reduce the racemic β-keto amides. The unreacted enantiomers were separated from the β-hydroxy amides, the amides cleaved, and the extent of resolution was determined for the cyclic amines. Detailed experimental and spectral data are provided for all compounds.
6 citations