ChemInform Abstract: Total Synthesis of Fluoxetine and Duloxetine Through an in situ Imine Formation/Borylation/Transimination and Reduction Approach.

ChemInform ◽  
2014 ◽  
Vol 46 (3) ◽  
pp. no-no
Author(s):  
Adam D. J. Calow ◽  
Elena Fernandez ◽  
Andrew Whiting
Keyword(s):  
Total Synthesis ◽  
Reduction Approach

Total synthesis of fluoxetine and duloxetine through an in situ imine formation/borylation/transimination and reduction approach

2014 ◽  
Vol 12 (32) ◽  
pp. 6121-6127 ◽  
Author(s):  
Adam D. J. Calow ◽  
Elena Fernández ◽  
Andrew Whiting
Keyword(s):  
Total Synthesis ◽  
Total Syntheses ◽  
Unsaturated Aldehydes ◽  
Catalytic Asymmetric ◽  
Reduction Approach

Efficient, catalytic, asymmetric total syntheses of both (R)-fluoxetine and (S)-duloxetine from α,β-unsaturated aldehydes are reported.

The Total Synthesis of Rhabdastrellic Acid A

2018 ◽  
Author(s):  
Yaroslav Boyko ◽  
Christopher Huck ◽  
David Sarlah
Keyword(s):  
Total Synthesis ◽  
Late Stage ◽  
Cross Coupling ◽  
Side Chains ◽  
General Strategy ◽  
Modular Approach ◽  
Linear Sequence ◽  
Generating Sequence ◽  
First Time

<div>The first total synthesis of rhabdastrellic acid A, a highly cytotoxic isomalabaricane triterpenoid, has been accomplished in a linear sequence of 14 steps from commercial geranylacetone. The prominently strained <i>trans-syn-trans</i>-perhydrobenz[<i>e</i>]indene core characteristic of the isomalabaricanes is efficiently accessed in a selective manner for the first time through a rapid, complexity-generating sequence incorporating a reductive radical polyene cyclization, an unprecedented oxidative Rautenstrauch cycloisomerization, and umpolung 𝛼-substitution of a <i>p</i>-toluenesulfonylhydrazone with in situ reductive transposition. A late-stage cross-coupling in concert with a modular approach to polyunsaturated side chains renders this a general strategy for the synthesis of numerous family members of these synthetically challenging and hitherto inaccessible marine triterpenoids.</div>

Intramolecular Michael Addition of N- and O-Centred Nucleophiles to Tethered Acrylates. The Role of Double-Bond Geometry in Controlling the Diastereo- selectivity of Cyclizations Leading to 2,6-Disubstituted Tetrahydropyrans and Piperidines.

1998 ◽  
Vol 51 (1) ◽  
pp. 9 ◽  
Author(s):  
Martin G. Banwell ◽  
Brett D. Bissett ◽  
Chinh T. Bui ◽  
Ha T. T. Pham ◽  
Gregory W. Simpson
Keyword(s):  
Double Bond ◽  
Total Synthesis ◽  
Michael Addition ◽  
Reductive Amination ◽  
Major Product ◽  
Enantioselective Synthesis ◽  
Cyclization Reactions ◽  
Glandular Secretion

The oxyanion derived from hydroxyacrylate E-(5) undergoes smooth intramolecular Michael addition to give the trans-2,6-disubstituted tetrahydropyran (7) as the major product of reaction. In contrast, the oxyanion obtained from isomer Z-(5) cyclizes to give the cis-2,6-disubstituted tetrahydropyran (6) as the major product. Such chemistry has been extended to the enantioselective synthesis of (+)-(6) the acquisition of which constitutes a formal total synthesis of acid (+)-(2), a constituent of the glandular secretion from the civet cat (Viverra civetta). Reductive amination of keto acrylate (12) affords an intermediate amine which cyclizes, in situ, to give the cis-2,6-disubstituted piperidine (26). Analogous treatment of compound (13) delivers the isomeric trans-2,6-disubstituted piperidine (27) as the exclusive product of reaction. Transition state structures have been proposed to account for the diastereoselectivities observed in all of the cyclization reactions.

scholarly journals Identification of a Hanford Waste Site for Initial Deployment of the In Situ Gaseous Reduction Approach

2000 ◽  
Author(s):  
Edward C Thornton ◽  
Kirk J Cantrell ◽  
James M Faurote ◽  
Terrance J Gilmore ◽  
Khris B Olsen ◽  
...  
Keyword(s):  
Waste Site ◽  
Gaseous Reduction ◽  
Reduction Approach

scholarly journals Catalyst-Controlled Regiodivergence in Rearrangements of Indole-Based Onium Ylides

2021 ◽  
Author(s):  
Vaishnavi Nair ◽  
Volga Kojasoy ◽  
Croix Laconsay ◽  
Dean Tantillo ◽  
Uttam Tambar
Keyword(s):  
Total Synthesis ◽  
Density Functional ◽  
Functional Group ◽  
Copper Catalyst ◽  
Indole Alkaloid ◽  
Functional Theory ◽  
Solvent Cage ◽  
Oxonium Ylides ◽  
Synthetic Intermediates

We have developed catalyst-controlled regiodivergent rearrangements of onium-ylides derived from indole substrates. Oxonium ylides formed <i>in situ</i> from substituted indoles selectively undergo [2,3]- and [1,2]-rearrangements in the presence of a rhodium and copper catalyst, respectively. The combined experimental and density functional theory (DFT) computational studies indicate divergent mechanistic pathways involving a metal-free ylide in the rhodium catalyzed reaction favoring [2,3]-rearrangement, and a metal-coordinated ion-pair in the copper catalyzed [1,2]-rearrangement that recombines in the solvent-cage. The application<br>of our methodology was demonstrated in the first total synthesis of the indole alkaloid (±)-sorazolon B, which enabled the stereochemical reassignment of the natural product. Further functional group transformations of the rearrangement products to generate valuable synthetic intermediates were also demonstrated.

A Short and Efficient Total Synthesis of (+)-Deoxoprosopinine via Diastereoselective Allylation of the Bicyclic N-Acyl Iminium Ion Formed in situ with a π-Nucleophile

Synlett ◽  
2012 ◽  
Vol 23 (19) ◽  
pp. 2814-2816 ◽  
Author(s):  
Palakodety Krishna ◽  
Palabindela Srinivas ◽  
Bonepally Reddy ◽  
Kakita Rao ◽  
Bharatam Jagadeesh
Keyword(s):  
Total Synthesis ◽  
Iminium Ion

An Approach to the Total Synthesis of Diterpenoid Plant Growth Substances Isolated From Gametophytes of the Fern Genus Anemia

1992 ◽  
Vol 45 (1) ◽  
pp. 227 ◽  
Author(s):  
CKF Chiu ◽  
LN Mander ◽  
AD Stuart ◽  
AC Willis
Keyword(s):  
Total Synthesis ◽  
Liquid Ammonia ◽  
Crystallographic Analysis ◽  
Aldol Reactions ◽  
Growth Substances ◽  
Enol Ether ◽  
X Ray ◽  
Relative Stereochemistry ◽  
Plant Growth Substances

Reduction of the oxoindan acid (9) by potassium in liquid ammonia followed by in situ alkylation with 3-methylbut-2-enyl bromide furnished enol ether (14) which was transformed into the acetal (17) and thence aldehydes (18; R = COCH3 and COCHCl2). Acid- catalysed aldol reactions then afforded the ethanoindene derivatives (19; R=COCH3 and COCHCl2). Further elaboration gave carbinol (28) which is envisaged as an intermediate for the total synthesis of the diterpenoid antheridiogens obtained from gametophytes of the fern genus Anemia, including acid (2). The relative stereochemistry of acetal (17) was established by X-ray crystallographic analysis.

scholarly journals Identification of a Hanford Waste Site for Initial Deployment of the In Situ Gaseous Reduction Approach

2000 ◽  
Author(s):  
Edward C. Thornton ◽  
Kirk J. Cantrell ◽  
James M. Faurote ◽  
Tyler J. Gilmore ◽  
Khris B. Olsen ◽  
...  
Keyword(s):  
Waste Site ◽  
Gaseous Reduction ◽  
Reduction Approach

In situ preparation of multi-wall carbon nanotubes/Au composites for oxygen electroreduction

RSC Advances ◽  
2016 ◽  
Vol 6 (94) ◽  
pp. 91209-91215 ◽  
Author(s):  
Na Li ◽  
Zhenghua Tang ◽  
Likai Wang ◽  
Qiannan Wang ◽  
Wei Yan ◽  
...  
Keyword(s):  
Carbon Nanotubes ◽  
Oxygen Reduction Reaction ◽  
Oxygen Reduction ◽  
Reduction Reaction ◽  
Oxygen Electroreduction ◽  
Multi Wall Carbon Nanotubes ◽  
In Situ Preparation ◽  
Reduction Approach

Multi-wall carbon nanotubes (CNTs)/Au nanocomposites have been prepared by the in situ reduction approach for oxygen reduction reaction.

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