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

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

ChemInform ◽  
2003 ◽  
Vol 34 (6) ◽  
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.

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>

Concise Total Synthesis of Curvulone B

Synlett ◽  
2020 ◽  
Author(s):  
Debendra K. Mohapatra ◽  
Shivalal Banoth ◽  
Utkal Mani Choudhury ◽  
Kanakaraju Marumudi ◽  
Ajit C. Kunwar
Keyword(s):  
Total Synthesis ◽  
Stereoselective Synthesis ◽  
Ring System ◽  
Bond Forming ◽  
Cross Metathesis ◽  
Bond Forming Reactions ◽  
Key Steps

AbstractA concise and convergent stereoselective synthesis of curvulone B is described. The synthesis utilized a tandem isomerization followed by C–O and C–C bond-forming reactions following Mukaiyama-type aldol conditions for the construction of the trans-2,6-disubstituted dihydropyran ring system as the key steps. Other important features of this synthesis are a cross-metathesis, epimerization, and Friedel–Crafts acylation.

ChemInform Abstract: TOTAL SYNTHESIS OF THE 6-SILASTEROID RING SYSTEM

1975 ◽  
Vol 6 (52) ◽  
pp. no-no
Author(s):  
S. BARCZA ◽  
C. W. HOFFMAN
Keyword(s):  
Total Synthesis ◽  
Ring System

scholarly journals Short, enantioselective, gram-scale synthesis of (−)-zephyranthine

2021 ◽  
Author(s):  
Yuxiang Zhao ◽  
Yanren Zhu ◽  
Guolan Ma ◽  
Qi Wei ◽  
Shaoxiong Yang ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Functional Group ◽  
Ring System ◽  
System Construction ◽  
Synthesis Design

A reasonable synthesis design by strategically integrating functional group manipulation into the ring system construction resulted in a short, enantioselective, gram-scale total synthesis of (−)-zephyranthine.

scholarly journals Stereoselective total syntheses of (±)-sinularene and (±)-5-epi-sinularene: a general intramolecular Diels–Alder approach to tricyclic sesquiterpenes

1985 ◽  
Vol 63 (4) ◽  
pp. 993-995 ◽  
Author(s):  
Kazimierz Antczak ◽  
John F. Kingston ◽  
Alex G. Fallis
Keyword(s):  
Double Bond ◽  
Methyl Ester ◽  
Total Synthesis ◽  
Ring System ◽  
Diels Alder ◽  
Exocyclic Double Bond ◽  
Total Syntheses ◽  
Methyl Group ◽  
Secondary Hydroxyl ◽  
Selective Hydrogenolysis

Stereoselective total synthesis of (±)-sinularene and (±)-5-epi-sinularene are described. The sequence employs a "blocked" cyclopentadiene in which the cyclopropane unit also serves as a latent methyl group. Thus intramolecular [4 + 2] cycloaddition of the substituted methyl spiro[2.4]hepta-4,6-dien-1-yl)-2-pentenoate 11 affords 5-benzyloxy-6-isopropyl-8-carbomethoxytetracyclo[5.4.01,7.02,4.02,9]undec-10-ene (12) which after selective hydrogenolysis generates the tricyclo[4.4.01,6.02,8]decane (sinularene) ring system. Removal of the secondary hydroxyl function (Ph3P/CCl4/CH3CN; H2/Pd/C), reduction of the methyl ester (LiAlH4), and introduction of the exocyclic double bond (acetate pyrolysis, 550 °C) completes the synthesis of (±)-sinularene in 14 steps from cyclopentadiene. A parallel series of reactions employing the isopropyl epimer of 12 affords (±)-5-epi-sinularene.

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
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