scholarly journals Synthesis of indole-based propellane derivatives via Weiss–Cook condensation, Fischer indole cyclization, and ring-closing metathesis as key steps

2013 ◽  
Vol 9 ◽  
pp. 2709-2714 ◽  
Author(s):  
Sambasivarao Kotha ◽  
Ajay Kumar Chinnam ◽  
Arti Tiwari
Keyword(s):  
Ring Closing Metathesis ◽  
Key Steps

A variety of highly functionalized indole-based [n.3.3]propellane derivatives is described. The synthesis of the propellane derivatives involves a Weiss–Cook condensation, a Fischer indole cyclization, and a ring-closing metathesis as key steps.

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 A short stereoselective synthesis of (+)-(6R,2′S)-cryptocaryalactone via ring-closing metathesis

2009 ◽  
Vol 5 ◽  
Author(s):  
Palakodety Radha Krishna ◽  
Krishnarao Lopinti ◽  
K L N Reddy
Keyword(s):  
Stereoselective Synthesis ◽  
Metathesis Reaction ◽  
Ring Closing Metathesis ◽  
Propargylic Alcohol ◽  
Key Steps

A short stereoselective synthesis of (+)-(6R,2′S)-cryptocaryalactone was successfully completed. Key steps included the application of Carreira’s asymmetric alkynylation reaction to form a propargylic alcohol and subsequently lactone formation using the powerful ring-closing metathesis reaction.

Ring-Closing Metathesis Approach to Cage Propellanes Containing Oxepane and Tetrahydrofuran Hybrid System

Synthesis ◽  
2017 ◽  
Vol 49 (24) ◽  
pp. 5339-5350 ◽  
Author(s):  
Sambasivarao Kotha ◽  
Subba Cheekatla ◽  
Darshan Mhatre
Keyword(s):  
Claisen Rearrangement ◽  
Alder Reaction ◽  
Diels Alder ◽  
Ring Closing Metathesis ◽  
Cage Compounds ◽  
Transannular Cyclization ◽  
Diels Alder Reaction ◽  
Grignard Addition ◽  
Key Steps ◽  
First Time

The preparation of a variety of structurally interesting oxygenated cage compounds involving atom-economic processes such as Claisen rearrangement, Diels–Alder reaction, [2+2] photocycloaddition, and ring-closing metathesis (RCM) as key steps is reported. For the first time, oxepane ring system is introduced in cage framework using olefin metathesis as a key step. These cage systems assembled here are difficult to prepare by traditional methods. The synthetic sequence described here opens up new routes to higher order polycycles containing heteroatoms without the involvement of protecting groups. Transannular cyclization observed during Grignard addition and the RCM protocol used here may be applicable to generate unknown oxygenated cage systems.

Stereoselective Total Syntheses of (3R,5R)-Sonnerlactone and (3R,5S)-Sonnerlactone

2017 ◽  
Vol 12 (9) ◽  
pp. 1934578X1701200
Author(s):  
Supriya Ghanty ◽  
P. Rasvan Khan ◽  
B. V. Subba Reddy
Keyword(s):  
Malic Acid ◽  
Ring Closing Metathesis ◽  
Total Syntheses ◽  
Key Steps ◽  
Barbier Allylation

A highly convergent and concise total syntheses of (3 R,5 R)-Sonnerlactone and (3 R,5 S) Sonnerlactone from a readily available L-malic acid is described. The following series of reactions such as Barbier allylation, photochemical esterification and Ring Closing Metathesis (RCM) are utilized as key steps to accomplish their syntheses.

scholarly journals Stereoselective Total Synthesis of (6S)-5,6-Dihydro-6-[(2R)-2-hydroxy-6-phenylhexyl]-2H-pyran-2-one from L-Malic Acid

2018 ◽  
Vol 13 (7) ◽  
pp. 1934578X1801300
Author(s):  
Dandekar Chandrakanth ◽  
Yerragorla Gopala Rao ◽  
Tallapally Swamy ◽  
Dhanraj O Biradar ◽  
Lonavath Vishnupriya ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Malic Acid ◽  
Ring Closing Metathesis ◽  
Stereoselective Reduction ◽  
Key Steps ◽  
Barbier Allylation

A stereoselective total synthesis of an antiproliferative and antifungal natural product, (6 S)-5,6-dihydro-6-[(2 R)-2-hydroxy-6-phenylhexyl]-2 H-pyran-2-one has been accomplished using the Barbier allylation, LiAlH4/LiI mediated syn-stereoselective reduction and olefin ring-closing metathesis (RCM) as the key steps. L-Malic acid was used as a chiral precursor for the construction of syn-1,3-diol moiety of the molecule.

scholarly journals A Concise and Stereoselective Total Synthesis of Paecilomycin E

2019 ◽  
Vol 14 (1) ◽  
pp. 1934578X1901400
Author(s):  
A. Srinivas Reddy ◽  
Gundamalla Bhavani ◽  
Sandhya Jonnala ◽  
Rajashaker Bantu ◽  
B. V. Subba Reddy
Keyword(s):  
Total Synthesis ◽  
Ring Closing Metathesis ◽  
Key Steps ◽  
Acid Unit

A concise approach for the first total synthesis of paecilomycin E is described involving Alder-Rickert reaction, Mitsunobu esterification and ring closing metathesis as the key steps. This approach has successfully demonstrated the Alder-Rickert protocol for the construction of resorcylic acid unit.

Synthesis of Carbocyclic Nucleosides (+)-Neplanocin A, (+)-Aristeromycin and 4'-epi-(+)-Aristeromycin from D-Fructose

2019 ◽  
Vol 16 (9) ◽  
pp. 750-758
Author(s):  
Perali R. Sridhar ◽  
Vennam D.K. Reddy ◽  
Mandava Suresh ◽  
Nadiveedhi M. Reddy ◽  
K. Shiva Kumar
Keyword(s):  
Total Synthesis ◽  
Allylic Alcohol ◽  
Starting Material ◽  
Carbocyclic Nucleosides ◽  
Ring Closing Metathesis ◽  
Neplanocin A ◽  
Oxidative Rearrangement ◽  
Key Steps

D-Fructose is used as the chiral pool starting material for the stereoselective total synthesis of (+)-neplanocin A. Zinc mediated fragmentation, ring-closing metathesis and oxidative rearrangement of cyclic tertiary allylic alcohol are used as the key steps in achieving the synthesis of key carbocylic intermediate. Further, stereoselective total synthesis of 4'-epi-(+)-aristeromycin and the conversion of (+)-neplanocin A to a mixture of (+)-aristeromycin and 4'-epi-(+)-aristeromycin are described.

Studies towards the Synthesis of the Pyrido[1,2-a]azepine Alkaloids

2021 ◽  
Vol 18 ◽  
Author(s):  
DauXuan Duc
Keyword(s):  
Ring Structure ◽  
Bicyclic Compound ◽  
Metathesis Reaction ◽  
Ring Closing Metathesis ◽  
Key Steps

A study towards the synthesis of the pyrido[1,2-a]azepine alkaloids is described. The bicyclic compound 1 containing the A-B core ring structure was synthesized in 17 steps in 1.7 % overall yield starting from 4-pentyn-1-ol. The key steps involve an oxidation of 1,4 diol to lactone and an ene-yne ring closing metathesis reaction.

Chiron approach for the total synthesis of brevipolide M

Synlett ◽  
2022 ◽  
Author(s):  
Yang Liu ◽  
Ziyang Zhao ◽  
Chao Hu ◽  
Chuanfang Zhao ◽  
Jun Liu ◽  
...  
Keyword(s):  
Double Bond ◽  
Total Synthesis ◽  
Stereoselective Synthesis ◽  
Ring Closing Metathesis ◽  
One Pot ◽  
Double Bond Migration ◽  
Key Steps

An efficient stereoselective synthesis of brevipolide M was established in 13 linear steps and 17.8% overall yields base on chiron approach. The key steps of our synthesis involved tandem homologation / tetrahydrofuran cyclization and sequential ring-closing metathesis (RCM) / double-bond migration in one-pot processes.

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