A stereoselective approach to indolizidine and pyrrolizidine alkaloids: total synthesis of (−)-lentiginosine, (−)-epi-lentiginosine and (−)-dihydroxypyrrolizidine

2014 ◽  
Vol 12 (25) ◽  
pp. 4454-4460 ◽  
Author(s):  
Shruti Vandana Kauloorkar ◽  
Vishwajeet Jha ◽  
Ganesh Jogdand ◽  
Pradeep Kumar
Keyword(s):  
Total Synthesis ◽  
Pyrrolizidine Alkaloids ◽  
Starting Material ◽  
Asymmetric Dihydroxylation ◽  
Key Steps

The total synthesis of (−)-lentiginosine, epi-1,2-lentiginosine and dihydroxypyrrolizidine is reported from an aldehyde as a starting material using organocatalysis and asymmetric dihydroxylation as key steps.

Concise asymmetric total synthesis of bruceolline J

2015 ◽  
Vol 2 (5) ◽  
pp. 548-551 ◽  
Author(s):  
Dattatraya H. Dethe ◽  
Vijay Kumar B
Keyword(s):  
Total Synthesis ◽  
Lewis Acid ◽  
Asymmetric Total Synthesis ◽  
Asymmetric Dihydroxylation ◽  
Key Steps

Concise biomimetic and asymmetric approach involving Sharpless asymmetric dihydroxylation and Lewis acid catalysed cyclopenta[b]annulation as key steps to synthesize (+)-bruceolline J.

scholarly journals The total synthesis of D-chalcose and its C-3 epimer

2013 ◽  
Vol 9 ◽  
pp. 2620-2624 ◽  
Author(s):  
Jun Sun ◽  
Song Fan ◽  
Zhan Wang ◽  
Guoning Zhang ◽  
Kai Bao ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Grignard Reaction ◽  
Efficient Synthesis ◽  
Camphorsulfonic Acid ◽  
Asymmetric Dihydroxylation ◽  
Key Steps ◽  
Stereogenic Center ◽  
Hydroxy Groups

We completed a new and efficient synthesis of D-chalcose (I) and the first synthesis of its C-3 epimer (I′) in nine steps with overall yields of 23% and 24%, respectively. The key steps in the sequence were the formation of the stereocenter on C3 via Grignard reaction, the introduction of the stereogenic center on C2 by Sharpless asymmetric dihydroxylation, the protection of the C1 and C2 hydroxy groups with tert-butyldimethylsilyl trifluoromethanesulfonate (TBSOTf), and the selective cleavage of the primary OTBS ether using catalytic DL-10-camphorsulfonic acid (CSA) in MeOH.

Total synthesis of (+)-monocerin via tandem dihydroxylation-SN2 cyclization and a copper mediated tandem cyanation–lactonization approach

2014 ◽  
Vol 12 (31) ◽  
pp. 5973-5980 ◽  
Author(s):  
U. Nookaraju ◽  
Eeshwaraiah Begari ◽  
Pradeep Kumar
Keyword(s):  
Total Synthesis ◽  
Asymmetric Dihydroxylation ◽  
Novel Synthesis ◽  
Key Steps ◽  
Julia Olefination

A simple and novel synthesis of (+)-monocerin was achieved from 3-buten-1-ol employing HKR, Julia olefination, intramolecular tandem Sharpless asymmetric dihydroxylation-SN2 cyclization and a novel copper mediated tandem cyanation–cyclization as the key steps.

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.

scholarly journals First total synthesis of mariamide A

2019 ◽  
Vol 44 (1-2) ◽  
pp. 114-120
Author(s):  
Yamu Xia ◽  
Chenglong Chen ◽  
Mengying Li ◽  
Weizeng Zhou ◽  
Shuyu Sun ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Nucleophilic Substitution ◽  
Starting Material ◽  
Potential Utility ◽  
Antidiabetic Agent ◽  
Silybum Marianum ◽  
Sequential Elimination ◽  
Group A ◽  
Key Steps

Mariamide A, a lignanamide isolated from the seeds of Silybum marianum, has demonstrated potential utility as an antioxidant and antidiabetic agent and possesses an 8-O-4′ neolignan skeleton. Herein, a first total synthesis of mariamide A is presented that proceeds in nine steps using vanillin as the starting material. The key steps for the preparation of mariamide A involve an I2-catalyzed bromomethoxylation of an alkene group, a nucleophilic substitution followed by a sequential elimination and a monoacylation reaction.

A Chemoenzymatic Total Synthesis of the Undecenolide ( - )-Cladospolide C

2005 ◽  
Vol 58 (7) ◽  
pp. 511 ◽  
Author(s):  
Martin G. Banwell ◽  
David T. J. Loong ◽  
Anthony C. Willis
Keyword(s):  
Total Synthesis ◽  
Single Crystal ◽  
Natural Product ◽  
Absolute Configuration ◽  
Starting Material ◽  
Unsaturated Ester ◽  
Ring Closing Metathesis ◽  
X Ray ◽  
Key Steps ◽  
First Time

The (−)-enantiomer, ent-3, of the natural product (+)-cladospolide C (3) has been prepared for the first time using the monochiral cis-1,2-dihydrocatechol 5 as starting material. Key steps include coupling of the derived acid 6 with the enzymatically generated (S)-(+)-4-penten-2-ol (7) and ring-closing metathesis (RCM) of the resultant doubly unsaturated ester 8 to give lactone 9. The structure of this last compound has been confirmed by single-crystal X-ray analysis. This work has established that the absolute configuration of (+)-cladospolide C has been correctly assigned and is as illustrated in structure 3.

Enantioselective first total synthesis of eujavanoic acid B through organocatalyzed IMDA reaction

RSC Advances ◽  
2015 ◽  
Vol 5 (19) ◽  
pp. 14465-14469 ◽  
Author(s):  
Jayprakash Narayan Kumar ◽  
Biswanath Das
Keyword(s):  
Total Synthesis ◽  
Starting Material ◽  
Asymmetric Allylation ◽  
Key Steps ◽  
Julia Olefination

The first total synthesis of the polyketide eujavanoic acid B has been accomplished using 1,3-propane diol as the starting material and involving Maruoka asymmetric allylation, Julia olefination, HWE olefination and organocatalyzed IMDA reaction as the key steps.

Total synthesis of wikstrol A and wikstrol B

2019 ◽  
Vol 17 (35) ◽  
pp. 8206-8213 ◽  
Author(s):  
Kui Lu ◽  
Ming Li ◽  
Yuna Huang ◽  
Yuanyuan Sun ◽  
Zhi Gong ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Oxidative Coupling ◽  
Asymmetric Dihydroxylation ◽  
Key Steps

The first total synthesis of wikstrol A and wikstrol B was achieved via Sharpless asymmetric dihydroxylation, Sonogashira and rhodium-catalyzed oxidative coupling as key steps.

Recent advances on the synthesis of the antidepressant Paroxetine

2020 ◽  
Vol 27 ◽  
Author(s):  
Joana Santos ◽  
M. Fernanda Proença ◽  
Ana Joao Rodrigues ◽  
Patricia Patrício ◽  
H. Sofia Domingues
Keyword(s):  
Total Synthesis ◽  
Neurological Disorders ◽  
Serotonin Reuptake ◽  
Potent Inhibitor ◽  
Starting Material ◽  
Substitution Pattern ◽  
Biological Probes ◽  
Recent Advances ◽  
Treatment Of Depression ◽  
Made In

: Paroxetine is a potent inhibitor of serotonin reuptake and is widely prescribed for the treatment of depression and other neurological disorders. The synthesis of paroxetine and the possibility to prepare derivatives with a specific substitution pattern that may allow their use as biological probes, is an attractive topic especially for medicinal chemists engaged in neurosciences research. Considering the extensive work that was developed in the last decade on the total synthesis of paroxetine, this review summarizes the most important contributions in this field, organized according to the reagent that was used as starting material. Most of the methods allowed to prepare paroxetine in 4-9 steps with an overall yield of 9-66%. Despite the progress made in this area, there is still room for improvement, searching for new eco-friendly and sustainable synthetic alternatives.

Concise Total Synthesis of Curvulone B

Synlett ◽  
2020 ◽  
Author(s):  
Debendra K. Mohapatra ◽  
Shivalal Banoth ◽  
Utkal Mani Choudhury ◽  
Kanakaraju Marumudi ◽  
Ajit C. Kunwar
Keyword(s):  
Total Synthesis ◽  
Stereoselective Synthesis ◽  
Ring System ◽  
Bond Forming ◽  
Cross Metathesis ◽  
Bond Forming Reactions ◽  
Key Steps

AbstractA concise and convergent stereoselective synthesis of curvulone B is described. The synthesis utilized a tandem isomerization followed by C–O and C–C bond-forming reactions following Mukaiyama-type aldol conditions for the construction of the trans-2,6-disubstituted dihydropyran ring system as the key steps. Other important features of this synthesis are a cross-metathesis, epimerization, and Friedel–Crafts acylation.

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