General Strategy toward the Tetrahydronaphthalene Skeleton. An Expedient Total Synthesis of Sertraline

1997 ◽  
Vol 62 (16) ◽  
pp. 5246-5247 ◽  
Author(s):  
Mark Lautens ◽  
Tomislav Rovis
Keyword(s):  
Total Synthesis ◽  
General Strategy

A One-Pot Chemoenzymatic Synthesis of (2S,4R)-4-Methylproline Enables the First Total Synthesis of Antiviral Lipopeptide Cavinafungin B

2018 ◽  
Author(s):  
Christian R. Zwick ◽  
Hans Renata
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Complex Molecule ◽  
Molecular Target ◽  
Chemoenzymatic Synthesis ◽  
General Strategy ◽  
One Pot

We report an efficient ten-step synthesis of antiviral natural product cavinafungin B in 37% overall yield. By leveraging a one-pot chemoenzymatic synthesis of (2S,4R)-4-methylproline and oxazolidine-tethered (Rink-Boc-ATG-resin) SPPS methodology, the assembly of our molecular target could be conducted in an efficient manner.This general strategy could prove amenable to the construction of other natural and unnatural linear lipopeptides. The value of incorporating biocatalytic steps in complex molecule synthesis is highlighted by this work.

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>

ChemInform Abstract: Total Synthesis of Both (+)-Compactin and (+)-Mevinolin. A General Strategy Based on the Use of a Special TiCl3/C8K Mixture for Dicarbonyl Coupling.

ChemInform ◽  
1989 ◽  
Vol 20 (3) ◽  
Author(s):  
D. L. J. CLIVE ◽  
K. S. K. MURTHY ◽  
A. G. H. WEE ◽  
J. S. PRASAD ◽  
G. V. J. DA SILVA ◽  
...  
Keyword(s):  
Total Synthesis ◽  
General Strategy

Studies Towards the Total Synthesis of Cycloaraneosene and Ophiobolin M: A General Strategy for the Construction of the 5−8 Bicyclic Ring System

2002 ◽  
Vol 2002 (18) ◽  
pp. 3145-3152 ◽  
Author(s):  
Parminder K. Ruprah ◽  
Jean-Philippe Cros ◽  
J. Elizabeth Pease ◽  
William G Whittingham ◽  
Jonathan M. J. Williams
Keyword(s):  
Total Synthesis ◽  
Ring System ◽  
General Strategy

A One-Pot Chemoenzymatic Synthesis of (2S,4R)-4-Methylproline Enables the First Total Synthesis of Antiviral Lipopeptide Cavinafungin B

2018 ◽  
Author(s):  
Christian R. Zwick ◽  
Hans Renata
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Complex Molecule ◽  
Molecular Target ◽  
Chemoenzymatic Synthesis ◽  
General Strategy ◽  
One Pot

We report an efficient ten-step synthesis of antiviral natural product cavinafungin B in 37% overall yield. By leveraging a one-pot chemoenzymatic synthesis of (2S,4R)-4-methylproline and oxazolidine-tethered (Rink-Boc-ATG-resin) SPPS methodology, the assembly of our molecular target could be conducted in an efficient manner.This general strategy could prove amenable to the construction of other natural and unnatural linear lipopeptides. The value of incorporating biocatalytic steps in complex molecule synthesis is highlighted by this work.

General Strategy for the Construction of Enantiopure Pyrrolidine-Based Alkaloids. Total Synthesis of (−)-Monomorine

2007 ◽  
Vol 72 (8) ◽  
pp. 3133-3136 ◽  
Author(s):  
Suhong Zhang ◽  
Liang Xu ◽  
Lei Miao ◽  
Hong Shu ◽  
Mark L. Trudell
Keyword(s):  
Total Synthesis ◽  
General Strategy

scholarly journals General Strategy for the Construction of Enantiopure Pyrrolidine-Based Alkaloids. Total Synthesis of (—)-Monomorine.

ChemInform ◽  
2007 ◽  
Vol 38 (35) ◽  
Author(s):  
Suhong Zhang ◽  
Liang Xu ◽  
Lei Miao ◽  
Hong Shu ◽  
Mark L. Trudell
Keyword(s):  
Total Synthesis ◽  
General Strategy
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