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.

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.

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

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.

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.

Asymmetric total synthesis of (+)-ovafolinins A and B

2018 ◽  
Vol 54 (54) ◽  
pp. 7539-7541
Author(s):  
Xianhe Fang ◽  
Lei Shen ◽  
Xiangdong Hu
Keyword(s):  
Total Synthesis ◽  
Oxidative Cyclization ◽  
Synthetic Approach ◽  
Asymmetric Total Synthesis

Benefiting from a highly diastereoselective alkylation of (S)-Taniguchi lactone, a double Friedel–Crafts reaction, a global debenzylation and a Cu(OAc)2-enabled benzylic oxidative cyclization, an efficient synthetic approach to (+)-ovafolinins A and B has been developed.

General Cyclopropane Assembly via Enantioselective Redox-Active Carbene Transfer to Aliphatic Olefins

2018 ◽  
Author(s):  
Marc Montesinos-Magraner ◽  
Matteo Costantini ◽  
Rodrigo Ramirez-Contreras ◽  
Michael E. Muratore ◽  
Magnus J. Johansson ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Asymmetric Synthesis ◽  
Chemical Space ◽  
Synthetic Approach ◽  
Asymmetric Cyclopropanation ◽  
Redox Active ◽  
Wide Range ◽  
Leaving Group ◽  
Stereoelectronic Properties ◽  
Carbene Transfer

Asymmetric cyclopropane synthesis currently requires bespoke strategies, methods, substrates and reagents, even when targeting similar compounds. This limits the speed and chemical space available for discovery campaigns. Here we introduce a practical and versatile diazocompound, and we demonstrate its performance in the first unified asymmetric synthesis of functionalized cyclopropanes. We found that the redox-active leaving group in this reagent enhances the reactivity and selectivity of geminal carbene transfer. This effect enabled the asymmetric cyclopropanation of a wide range of olefins including unactivated aliphatic alkenes, enabling the 3-step total synthesis of (–)-dictyopterene A. This unified synthetic approach delivers high enantioselectivities that are independent of the stereoelectronic properties of the functional groups transferred. Our results demonstrate that orthogonally-differentiated diazocompounds are viable and advantageous equivalents of single-carbon chirons<i>.</i>

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