Formal Synthesis of (±)-Aplykurodinone-1 Based on the Indium-Catalyzed Conia-Ene Reaction

Synlett ◽  
2020 ◽  
Vol 31 (14) ◽  
pp. 1404-1408
Author(s):  
Xiaoji Wang ◽  
Liping Wang ◽  
Shuangping Huang ◽  
Yi Zhou ◽  
Hesheng Xiao ◽  
...  
Keyword(s):  
Conjugate Addition ◽  
Selenium Dioxide ◽  
Ring Closing Metathesis ◽  
Formal Synthesis ◽  
Ene Reaction ◽  
Synthetic Strategy

A concise formal synthesis of (±)-aplykurodinone-1 starting from a commercially available material and based on the indium-catalyzed Conia-ene reaction has been accomplished. The synthesis features a Riley selenium dioxide oxidation, a Krapcho dealkoxycarbonylation, and a ring-closing metathesis approach. The synthetic strategy was also supported by a Saegusa oxidation and a classic Michael 1,4-conjugate addition.

scholarly journals Design and synthesis of hybrid cyclophanes containing thiophene and indole units via Grignard reaction, Fischer indolization and ring-closing metathesis as key steps

2015 ◽  
Vol 11 ◽  
pp. 1514-1519 ◽  
Author(s):  
Sambasivarao Kotha ◽  
Ajay Kumar Chinnam ◽  
Mukesh Eknathrao Shirbhate
Keyword(s):  
Grignard Reaction ◽  
Ring Closing Metathesis ◽  
Design And Synthesis ◽  
Synthetic Strategy ◽  
Fischer Indolization ◽  
Grignard Addition ◽  
Key Steps

We demonstrate a new synthetic strategy to cyclophanes containing thiophene and indole moieties via Grignard addition, Fischer indolization and ring-closing metathesis as key steps.

scholarly journals Bridgehead vicinal diallylation of norbornene derivatives and extension to propellane derivatives via ring-closing metathesis

2016 ◽  
Vol 12 ◽  
pp. 1877-1883 ◽  
Author(s):  
Sambasivarao Kotha ◽  
Rama Gunta
Keyword(s):  
Single Crystal ◽  
Diffraction Analysis ◽  
X Ray Diffraction ◽  
Ring Closing Metathesis ◽  
X Ray ◽  
Synthetic Strategy ◽  
Norbornene Derivatives

Here, we report a simple synthetic strategy to the bridgehead vicinal diallylation of norbornene derivatives. These substrates are useful to generate propellanes via ring-closing metathesis. Single-crystal X-ray diffraction analysis of four compounds led to the realization of configurational correction of earlier reported molecules.

Asymmetric synthesis of cyclic β-amino acids and cyclic amines via sequential diastereoselective conjugate addition and ring closing metathesis

Tetrahedron ◽  
2003 ◽  
Vol 59 (18) ◽  
pp. 3253-3265 ◽  
Author(s):  
Ann M Chippindale ◽  
Stephen G Davies ◽  
Keiji Iwamoto ◽  
Richard M Parkin ◽  
Christian A.P Smethurst ◽  
...  
Keyword(s):  
Amino Acids ◽  
Asymmetric Synthesis ◽  
Conjugate Addition ◽  
Ring Closing Metathesis ◽  
Cyclic Amines

Towards the Total Synthesis of Schisandrene: Stereoselective Synthesis of the Dibenzocyclooctadiene Lignan Core

Synlett ◽  
2018 ◽  
Vol 29 (07) ◽  
pp. 908-911 ◽  
Author(s):  
K. Babu ◽  
Arramshetti Venkanna ◽  
Borra Poornima ◽  
Bandi Siva ◽  
B. Babu
Keyword(s):  
Total Synthesis ◽  
Stereoselective Synthesis ◽  
Asymmetric Reduction ◽  
Cross Coupling ◽  
Membered Ring ◽  
Stille Reaction ◽  
Reaction Sequence ◽  
Ring Closing Metathesis ◽  
Synthetic Strategy ◽  
First Time

A stereoselective synthesis of the dibenzocyclooctadiene ­lignan core of the natural product schisandrene is described. Starting from readily available gallic acid, the synthetic strategy involves Suzuki–Miyaura cross-coupling, Stille reaction, and ring-closing metathesis (RCM) in the reaction sequence. The required asymmetric center at C-7′ was established by an asymmetric reduction of a keto compound using the Corey–Bakshi–Shibata (CBS) catalyst. In our approach, the eight-membered ring was achieved by RCM for the first time.

Carbohydrate based formal synthesis of stemoamide using ring-closing metathesis

2002 ◽  
Vol 43 (2) ◽  
pp. 295-298 ◽  
Author(s):  
Mukund K Gurjar ◽  
Dandepally Srinivasa Reddy
Keyword(s):  
Ring Closing Metathesis ◽  
Formal Synthesis
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