Lipase-catalyzed domino kinetic resolution of α-hydroxynitrones/intramolecular 1,3-dipolar cycloaddition: a concise asymmetric total synthesis of (–)-rosmarinecine

2005 ◽  
pp. 2369 ◽  
Author(s):  
Shuji Akai ◽  
Kouichi Tanimoto ◽  
Yukiko Kanao ◽  
Sohei Omura ◽  
Yasuyuki Kita
Keyword(s):  
Total Synthesis ◽  
Kinetic Resolution ◽  
Dipolar Cycloaddition ◽  
Asymmetric Total Synthesis

scholarly journals Asymmetric total synthesis of rotenoids via organocatalyzed dynamic kinetic resolution

2019 ◽  
Vol 2 (1) ◽  
Author(s):  
Saima Perveen ◽  
Shuang Yang ◽  
Miao Meng ◽  
Weici Xu ◽  
Guoxiang Zhang ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Kinetic Resolution ◽  
Dynamic Kinetic Resolution ◽  
Asymmetric Total Synthesis

Dynamic Kinetic Resolution for the Catalytic Asymmetric Total Synthesis of Antithrombotic Agents M58163 and M58169

2007 ◽  
Vol 349 (4-5) ◽  
pp. 617-628 ◽  
Author(s):  
Fumihiko Saitoh ◽  
Hidemitsu Nishida ◽  
Takafumi Mukaihira ◽  
Kohsuke Aikawa ◽  
Koichi Mikami
Keyword(s):  
Total Synthesis ◽  
Kinetic Resolution ◽  
Dynamic Kinetic Resolution ◽  
Antithrombotic Agents ◽  
Asymmetric Total Synthesis ◽  
Catalytic Asymmetric

scholarly journals Facile generation of bridged medium-sized polycyclic systems by rhodium-catalysed intramolecular (3+2) dipolar cycloadditions

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Bao-Long Hou ◽  
Jonathan J. Wong ◽  
Na Lv ◽  
Yong-Qiang Wang ◽  
K. N. Houk ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Single Step ◽  
Bioactive Molecules ◽  
Dipolar Cycloaddition ◽  
General Strategy ◽  
Diastereoselective Synthesis ◽  
Asymmetric Total Synthesis ◽  
Ring Systems ◽  
Dipolar Cycloadditions ◽  
Unusual Type

AbstractBridged medium-sized bicyclo[m.n.2] ring systems are common in natural products and potent pharmaceuticals, and pose a great synthetic challenge. Chemistry for making bicyclo[m.n.2] ring systems remains underdeveloped. Currently, there are no general reactions available for the single-step synthesis of various bridged bicyclo[m.n.2] ring systems from acyclic precursors. Here, we report an unusual type II intramolecular (3+2) dipolar cycloaddition strategy for the syntheses of various bridged bicyclo[m.n.2] ring systems. This rhodium-catalysed cascade reaction provides a relatively general strategy for the direct and efficient regioselective and diastereoselective synthesis of highly functionalized and synthetically challenging bridged medium-sized polycyclic systems. Asymmetric total synthesis of nakafuran-8 was accomplished using this method as a key step. Quantum mechanical calculations demonstrate the mechanism of this transformation and the origins of its multiple selectivities. This reaction will inspire the design of the strategies to make complex bioactive molecules with bridged medium-sized polycyclic systems.

First Stereoselective Total Synthesis of Anti-Inflammatory Metabolite­ Penicillinolide A

Synthesis ◽  
2018 ◽  
Vol 51 (06) ◽  
pp. 1427-1434 ◽  
Author(s):  
Palakodety Krishna ◽  
Mopuri Reddy ◽  
Gembali Manikanta
Keyword(s):  
Total Synthesis ◽  
Kinetic Resolution ◽  
Asymmetric Allylation ◽  
Asymmetric Total Synthesis ◽  
Hydrolytic Kinetic Resolution ◽  
Anti Inflammatory ◽  
Key Steps

The first asymmetric total synthesis of penicillinolide A is described. Key steps of the synthesis involve Jacobsen’s hydrolytic kinetic resolution (HKR), chelation controlled allylation, Brown’s asymmetric allylation, hydroboration, and Yamaguchi lactonization.

scholarly journals Synthesis of acremines A, B and F and studies on the bisacremines

2019 ◽  
Vol 15 ◽  
pp. 2271-2276
Author(s):  
Nils Winter ◽  
Dirk Trauner
Keyword(s):  
Total Synthesis ◽  
Kinetic Resolution ◽  
Asymmetric Reduction ◽  
Asymmetric Total Synthesis

The acremines are a family of meroterpenoids isolated from fungi of the genus Acremonium. Here, we present the asymmetric total synthesis of acremine F which hinges on a modestly enantioselective dihydroxylation and a subsequent kinetic resolution via a highly selective asymmetric reduction. Chemoselective oxidation of acremine F gave access to acremines A and B. The dimerization of acremine F to bisacremine E was investigated but could not be achieved, shedding light on the formation of the acremine dimers in nature.

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