Concise asymmetric total synthesis of catunaregin

2016 ◽  
Vol 3 (9) ◽  
pp. 1084-1086 ◽  
Author(s):  
Hideki Abe ◽  
Takuma Hikichi ◽  
Kosuke Emori ◽  
Toyoharu Kobayashi ◽  
Hisanaka Ito
Keyword(s):  
Methyl Ester ◽  
Total Synthesis ◽  
Aldol Reaction ◽  
Asymmetric Total Synthesis ◽  
Acidic Conditions ◽  
Optically Pure

The asymmetric total synthesis of the optically pure catunaregin was accomplished in 7 steps from a known methyl ester using an asymmetric syn-selective aldol reaction and the successive ketalization of a furan diol derivative under acidic conditions.

Asymmetric Total Synthesis of (+)-Coprophilin

Synthesis ◽  
2017 ◽  
Vol 50 (06) ◽  
pp. 1301-1306 ◽  
Author(s):  
Isamu Shiina ◽  
Yuma Umezaki ◽  
Takatsugu Murata ◽  
Kyohei Suzuki ◽  
Takayuki Tonoi
Keyword(s):  
Total Synthesis ◽  
Aldol Reaction ◽  
Alder Reaction ◽  
Diels Alder ◽  
Core Structure ◽  
Asymmetric Total Synthesis ◽  
Diels Alder Reaction ◽  
Anticoccidial Agent

In this paper, we report the first total synthesis of (+)-coprophilin, an anticoccidial agent, by constructing the chiral linear precursor via a Mukaiyama–Evans aldol reaction and a stereoselective intramolecular Diels–Alder reaction. The proposed method can be used to provide large amounts of (+)-coprophilin, which exhibits a 3,4,5,6,7-pentasubstituted Δ1,2-octalin core structure.

Bioinspired total synthesis of (−)-gymnothelignan L

2018 ◽  
Vol 5 (7) ◽  
pp. 1124-1128 ◽  
Author(s):  
Peng Chen ◽  
Liang Huo ◽  
Huilin Li ◽  
Lin Liu ◽  
Ziyun Yuan ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Aldol Reaction ◽  
Synthetic Approach ◽  
Asymmetric Total Synthesis

The first asymmetric total synthesis of gymnothelignan L has been accomplished in 14 steps with 11.2% overall yield. The synthetic approach features an anti Evans aldol reaction, a diastereoselective methylation, a Suzuki–Miyaura coupling and a bioinspired desymmetric transannular Friedel–Crafts reaction.

ChemInform Abstract: An Asymmetric Total Synthesis of a Potent Immunosuppressant, Mycestericins D and F, Through an Aldol Reaction Using L-Threonine Aldolase.

ChemInform ◽  
2010 ◽  
Vol 31 (30) ◽  
pp. no-no
Author(s):  
Kiyoharu Nishide ◽  
Kayoko Shibata ◽  
Tetsuro Fujita ◽  
Tetsuya Kajimoto ◽  
Chi-Huey Wong ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Aldol Reaction ◽  
Asymmetric Total Synthesis ◽  
Threonine Aldolase

A concise asymmetric synthesis of (−)-trans-aerangis lactone

2018 ◽  
Vol 96 (12) ◽  
pp. 1061-1063 ◽  
Author(s):  
Rachana Pandey ◽  
Ranjana Prakash
Keyword(s):  
Ethylene Glycol ◽  
Total Synthesis ◽  
Asymmetric Synthesis ◽  
Aldol Reaction ◽  
Starting Material ◽  
Asymmetric Total Synthesis

A concise stereoselective approach to functionalized δ-lactone skeleton from monosilylated ethylene glycol as a starting material and its application to the asymmetric total synthesis of (−)-trans-aerangis lactone have been demonstrated. The synthesis utilizes the organocatalyzed MacMillan’s cross aldol reaction as a key step.

Asymmetric Total Synthesis of (-)-Azaspirene by Utilizing Ti-Claisen Condensation and Ti-Direct Aldol Reaction

2016 ◽  
Vol 2016 (28) ◽  
pp. 4834-4841 ◽  
Author(s):  
Mikiko Sugi ◽  
Ryohei Nagase ◽  
Tomonori Misaki ◽  
Hidefumi Nakatsuji ◽  
Yoo Tanabe
Keyword(s):  
Total Synthesis ◽  
Aldol Reaction ◽  
Asymmetric Total Synthesis ◽  
Claisen Condensation ◽  
Direct Aldol Reaction

scholarly journals Recent progress in organocatalytic asymmetric total syntheses of complex indole alkaloids

2017 ◽  
Vol 4 (3) ◽  
pp. 381-396 ◽  
Author(s):  
Jin Song ◽  
Dian-Feng Chen ◽  
Liu-Zhu Gong
Keyword(s):  
Total Synthesis ◽  
Multiple Bond ◽  
Indole Alkaloids ◽  
Cascade Reactions ◽  
Pharmaceutical Products ◽  
Chiral Molecules ◽  
Asymmetric Total Synthesis ◽  
Total Syntheses ◽  
Asymmetric Organocatalysis ◽  
Optically Pure

Abstract Indole and its structural analogues have been frequently found in numerous alkaloids, pharmaceutical products and related materials. The enantioselective construction of these structures allows efficient total synthesis of optically pure indole alkaloids, and hence has received worldwide interest. In the past decade, asymmetric organocatalysis has been recognized as one of the most powerful strategies to create chiral molecules with high levels of stereoselectivity. In particular, organocatalytic asymmetric cascade reactions often occur with multiple bond-breaking and forming events simultaneously or sequentially, leading to the appearance of various straightforward approaches to access core structures for asymmetric total synthesis. This review will summarize recent applications of asymmetric organocatalysis in the enantioselective synthesis of indole alkaloids.

scholarly journals Asymmetric total synthesis of smyrindiol employing an organocatalytic aldol key step

2012 ◽  
Vol 8 ◽  
pp. 1112-1117 ◽  
Author(s):  
Dieter Enders ◽  
Jeanne Fronert ◽  
Tom Bisschops ◽  
Florian Boeck
Keyword(s):  
Total Synthesis ◽  
Asymmetric Synthesis ◽  
Aldol Reaction ◽  
Asymmetric Total Synthesis

The first organocatalytic asymmetric synthesis of smyrindiol, by using an (S)-proline catalyzed enantioselective intramolecular aldol reaction as the key step, is described. Smyrindiol was synthesized from commercially available 2,4-dihydroxybenzaldehyde in 15 steps, with excellent stereoselectivity (de = 99%, ee = 99%). In the course of this total synthesis a new and mild coumarin assembly was developed.

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