Efficient Synthesis of Benzofurans Utilizing [3,3]-Sigmatropic Rearrangement Triggered byN-Trifluoroacetylation of Oxime Ethers: Short Synthesis of Natural 2-Arylbenzofurans

2007 ◽  
Vol 2007 (9) ◽  
pp. 1491-1509 ◽  
Author(s):  
Norihiko Takeda ◽  
Okiko Miyata ◽  
Takeaki Naito
Keyword(s):  
Sigmatropic Rearrangement ◽  
Efficient Synthesis ◽  
Short Synthesis

scholarly journals Simple and efficient synthesis of bicyclic enol-carbamates: access to brabantamides and their analogues

RSC Advances ◽  
2020 ◽  
Vol 10 (12) ◽  
pp. 6790-6793
Author(s):  
Ondrej Záborský ◽  
Ľudmila Petrovičová ◽  
Jana Doháňošová ◽  
Ján Moncol ◽  
Róbert Fischer
Keyword(s):  
Efficient Synthesis ◽  
Short Synthesis

A simple and short synthesis of bicyclic enol-carbamates with high E/Z selectivity and the synthesis of brabantamide A analogue are presented.

A short synthesis of both enantiomers of enterolactone

2000 ◽  
Vol 78 (1) ◽  
pp. 133-138 ◽  
Author(s):  
Mukund P Sibi ◽  
Pingrong Liu ◽  
Michael D Johnson
Keyword(s):  
Key Words ◽  
Enantioselective Synthesis ◽  
Efficient Synthesis ◽  
Short Synthesis

A short and efficient synthesis of both enantiomers of enterolactone, a mammalian lignan, is described. The overall yield for the natural enterolactone, over seven steps, was 19% and for its enantiomer 27%. Key words: enterolactone, 4-diphenylmethyl-2-oxazolidinone, succinate, enantioselective synthesis.

scholarly journals Total Synthesis of Nine Longiborneol Sesquiterpenoids Using a Functionalized Camphor Strategy

2021 ◽  
Author(s):  
Robert F. Lusi ◽  
Goh Sennari ◽  
Richmond Sarpong
Keyword(s):  
Chemical Synthesis ◽  
Total Synthesis ◽  
Natural Product ◽  
Late Stage ◽  
Strategy Development ◽  
Topological Complexity ◽  
Efficient Synthesis ◽  
Short Synthesis ◽  
Synthesis Routes ◽  
The 1960S

<p>Natural product total synthesis inspires strategy development in chemical synthesis. In the 1960s, Corey and coworkers demonstrated a visionary preparation of the terpenoid longifolene, using “strategic bond analysis” to craft a synthesis route. This approach proposes that efficient synthesis routes to bridged, polycyclic, structures should be formulated to introduce the bulk of the target’s topological complexity at a late stage. In subsequent decades, similar strategies have proved general for the syntheses of a wide variety of bridged, polycyclic molecules. Here, we demonstrate that an orthogonal strategy, which utilizes a topologically complex bicyclo[2.2.1] starting material accessed through a scaffold rearrangement of (<i>S</i>)-carvone, leads to a remarkably short synthesis of the longifolene-related terpenoid longiborneol. We also employ a variety of late-stage C–H functionalization tactics in divergent syntheses of many longiborneol congeners. Our strategy should prove effective for the preparation of other topologically complex natural products that contain the bicyclo[2.2.1] framework.</p>

Efficient Synthesis of Indoles Using [3,3]-Sigmatropic Rearrangement of N-Trifluoroacetyl Enehydrazines.

ChemInform ◽  
2006 ◽  
Vol 37 (32) ◽  
Author(s):  
Okiko Miyata ◽  
Norihiko Takeda ◽  
Yasuo Kimura ◽  
Yoshiji Takemoto ◽  
Norimitsu Tohnai ◽  
...  
Keyword(s):  
Sigmatropic Rearrangement ◽  
Efficient Synthesis
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