scholarly journals Total synthesis and complete configurational assignment of amphirionin-2

2021 ◽  
Author(s):  
Shota Kato ◽  
Daichi Mizukami ◽  
Tomoya Sugai ◽  
Masashi Tsuda ◽  
Haruhiko Fuwa
Keyword(s):  
Total Synthesis ◽  
Absolute Configuration ◽  
Late Stage ◽  
Type Reaction ◽  
Configurational Assignment

An extensive application of cobalt-catalyzed Mukaiyama-type cyclization of γ-hydroxy olefins and a late-stage Stille-type reaction enabled syntheses of four diastereomers of amphirionin-2 to establish its absolute configuration.

scholarly journals Synthesis and Configurational Assignment of Vinyl Sulfoximines and Sulfonimidamides

2021 ◽  
Author(s):  
Gregory Craven ◽  
Edward L. Briggs ◽  
Charlotte Zammit ◽  
Alex McDermott ◽  
Stephanie Greed ◽  
...  
Keyword(s):  
Absolute Configuration ◽  
Late Stage ◽  
Chemical Biology ◽  
Chemical Space ◽  
Protein Inhibitors ◽  
Electronic Circular Dichroism ◽  
Configurational Assignment ◽  
The Absolute ◽  
Synthetic Methodologies ◽  
Circular Dichroïsm

Vinyl sulfones and sulfonamides are valued for their use as electrophilic warheads in covalent protein inhibitors. Conversely, the S(VI) aza-isosteres thereof, vinyl sulfoximines and sulfonimidamides, are far less studied and have yet to be applied to the field of protein bioconjugation. Herein, we report a range of different synthetic methodologies for constructing vinyl sulfoximine and vinyl sulfonimidamide architectures that allows access to new areas of electrophilic chemical space. We demonstrate how late stage functionalization can be applied to these motifs to incorporate alkyne tags, generating fully functionalized probes for future chemical biology applications. Finally, we establish a workflow for determining the absolute configuration of enantioenriched vinyl sulfoximines and sulfonimidamides by comparing experimentally and computationally determined electronic circular dichroism spectra, enabling access to configurationally assigned enantiomeric pairs by separation.

Synthesis and absolute configuration assignment of albucidin: a late-stage reductive deiodination by visible light photocatalysis

2016 ◽  
Vol 14 (13) ◽  
pp. 3482-3485 ◽  
Author(s):  
Hu Zhang ◽  
Peng-Fei Liu ◽  
Qiong Chen ◽  
Qiong-You Wu ◽  
Anne Seville ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Visible Light ◽  
Absolute Configuration ◽  
Late Stage ◽  
Visible Light Photocatalysis ◽  
Configuration Assignment ◽  
Bioactive Molecule ◽  
The Way

The total synthesis and absolute configuration assignment of albucidin might pave the way for synthetic and medicinal chemists for further research on this type of bioactive molecule.

scholarly journals Synthesis and Configurational Assignment of Vinyl Sulfoximines and Sulfonimidamides

2021 ◽  
Author(s):  
Gregory Craven ◽  
Edward L. Briggs ◽  
Charlotte Zammit ◽  
Alex McDermott ◽  
Stephanie Greed ◽  
...  
Keyword(s):  
Absolute Configuration ◽  
Late Stage ◽  
Chemical Biology ◽  
Chemical Space ◽  
Protein Inhibitors ◽  
Electronic Circular Dichroism ◽  
Configurational Assignment ◽  
The Absolute ◽  
Synthetic Methodologies ◽  
Circular Dichroïsm

Vinyl sulfones and sulfonamides are valued for their use as electrophilic warheads in covalent protein inhibitors. Conversely, the S(VI) aza-isosteres thereof, vinyl sulfoximines and sulfonimidamides, are far less studied and have yet to be applied to the field of protein bioconjugation. Herein, we report a range of different synthetic methodologies for constructing vinyl sulfoximine and vinyl sulfonimidamide architectures that allows access to new areas of electrophilic chemical space. We demonstrate how late stage functionalization can be applied to these motifs to incorporate alkyne tags, generating fully functionalized probes for future chemical biology applications. Finally, we establish a workflow for determining the absolute configuration of enantioenriched vinyl sulfoximines and sulfonimidamides by comparing experimentally and computationally determined electronic circular dichroism spectra, enabling access to configurationally assigned enantiomeric pairs by separation.

Convergent Total Synthesis of Principinol D, a Rearranged Kaurane Diterpenoid

2019 ◽  
Author(s):  
Timothy Newhouse ◽  
Aneta Turlik ◽  
Yifeng Chen ◽  
Anthony Scruse
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Late Stage ◽  
Membered Ring ◽  
Entry Point ◽  
Ketone Reduction ◽  
Coupling Approach

<div> <p>The total synthesis of principinol D, a rearranged kaurane diterpenoid, is reported. This grayanane natural product is constructed via a convergent fragment coupling approach, wherein the central 7-membered ring is synthesized at a late stage. The bicyclo[3.2.1]octane fragment is accessed by a Ni-catalyzed α-vinylation reaction. Strategic reductions include a diastereoselective SmI<sub>2</sub>-mediated ketone reduction with PhSH and a new protocol for selective ester reduction in the presence of ketones. The convergent strategy reported herein may be an entry point to the larger class of kaurane diterpenoids.</p> </div>

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>

Asymmetric Total Synthesis and Determination of the Absolute Configuration of (+)-Srilankenyne via Sequence-Sensitive Halogenations Guided by Conformational Analysis

2021 ◽  
Vol 23 (4) ◽  
pp. 1321-1326
Author(s):  
Hongjun Jang ◽  
Soo Yeon Kwak ◽  
Dongjoo Lee ◽  
Juan V. Alegre-Requena ◽  
Hyoungsu Kim ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Conformational Analysis ◽  
Absolute Configuration ◽  
Asymmetric Total Synthesis ◽  
The Absolute
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