scholarly journals A Unified Total Synthesis of Isocyclocapitelline and Cyclocapitelline

2020 ◽  
Vol 15 (11) ◽  
pp. 1934578X2096787
Author(s):  
Marepally Srilatha ◽  
Vallabhareddy Satteyyanaidu ◽  
Chepyala Krishna Reddy ◽  
Venkata Subba Reddy Basireddy
Keyword(s):  
Total Synthesis ◽  
Ring Opening ◽  
Ring Opening Of Epoxide ◽  
Key Steps ◽  
Neutral Conditions ◽  
Intramolecular Ring

A facile and concise synthesis of β-carboline alkaloids, such as (–)-isocyclocapitelline and (+)-cyclocapitelline, has been achieved from commercially available geraniol through a unified strategy. The key steps involved in this synthesis are Sharpless epoxidation, intramolecular ring opening of epoxide, Pictet-Spengler reaction, and dehydrogenative aromatization using 10% palladium/carbon in xylene under neutral conditions.

scholarly journals Stereoselective Total Synthesis of 1,4-Dideoxy-1,4-imino-L-ribitol by an Intramolecular Ring Opening of Epoxide with a Tethered Amide

2018 ◽  
Vol 13 (8) ◽  
pp. 1934578X1801300 ◽  
Author(s):  
Chaya N Dhudmal ◽  
Dhanraj O Biradar ◽  
Maddipatla V. Satyanarayana ◽  
Basi V Subba Reddy
Keyword(s):  
Total Synthesis ◽  
Ring Opening ◽  
Amido Group ◽  
Ring Opening Of Epoxide ◽  
Intramolecular Ring

Stereoselective total synthesis of 1,4-dideoxy-1,4-imino-L-ribitol has been accomplished from D-glucose. The key step involved in this synthesis is the regioselective ring-opening of the epoxide with a tethered amido group to give the N-tosyl-3,6-dideoxy-3,6-imino-1,2- O-isopropylidene-α-D-glucofuranose.

First Total Synthesis of a Fluorinated Calystegin

2010 ◽  
Vol 65 (4) ◽  
pp. 445-451 ◽  
Author(s):  
René Csuk ◽  
Erik Prell ◽  
Stefan Reißmann ◽  
Claudia Korb
Keyword(s):  
Total Synthesis ◽  
Ring Opening ◽  
Competitive Inhibitor ◽  
Ring Closure ◽  
Target Compound ◽  
Metathesis Reaction ◽  
Grubbs Catalyst ◽  
Ring Opening Reaction ◽  
Ultrasound Assisted ◽  
Key Steps

A straightforward chiral pool synthesis for the first fluorinated calystegin is described. Key steps of this synthesis include an ultrasound-assisted Zn-mediated tandem ring opening reaction followed by a Grubbs’ catalyst-mediated ring closure metathesis reaction. The target compound is a selective and competitive inhibitor for a β -glycosidase.

First Stereoselective Synthesis of (6R,7R,8S)-8-Chlorogoniodiol

Synthesis ◽  
2017 ◽  
Vol 49 (11) ◽  
pp. 2483-2487 ◽  
Author(s):  
Ambati Sharada ◽  
Kundeti Rao ◽  
Jhillu Yadav ◽  
Tadikamalla Rao ◽  
Kommu Nagaiah
Keyword(s):  
Ring Opening ◽  
Stereoselective Synthesis ◽  
Asymmetric Epoxidation ◽  
Cinnamyl Alcohol ◽  
Linear Sequence ◽  
12 Steps ◽  
Ring Opening Of Epoxide ◽  
Key Steps ◽  
Sharpless Asymmetric Epoxidation ◽  
Barbier Allylation

A stereoselective synthesis of (6R,7R,8S)-8-chlorogoniodiol has been achieved in a linear sequence of 12 steps and 19.8% overall yield from cinnamyl alcohol. The key steps include Sharpless asymmetric epoxidation, regioselective ring opening of epoxide, indium-mediated Barbier allylation, and Still–Gennari olefination.

Total synthesis of (−)-depyranoversicolamide B

2015 ◽  
Vol 51 (89) ◽  
pp. 16143-16146 ◽  
Author(s):  
Wen-Fang Qin ◽  
T. Xiao ◽  
D. Zhang ◽  
Lin-Feng Deng ◽  
Y. Wang ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Ring Opening ◽  
Alder Reaction ◽  
Diels Alder ◽  
Asymmetric Total Synthesis ◽  
Diels Alder Reaction ◽  
Key Steps

Asymmetric total synthesis of (−)-depyranoversicolamide B (12) is described from easily prepared chiral pyrroloindoline 21. Key steps in the synthesis are reductive ring opening of the pyrrolo ring in 21 and stereoselective intramolecular Diels–Alder reaction of 18.

Studies on the Total Synthesis of Antibiotic Macrolactin S: A Conventional Approach for the Synthesis of the C1–C9 and C10–C24 Fragments

Synthesis ◽  
2017 ◽  
Vol 50 (03) ◽  
pp. 663-675
Author(s):  
Pabbaraja Srihari ◽  
Ramakrishna Sayini
Keyword(s):  
Total Synthesis ◽  
Nucleophilic Addition ◽  
Ring Opening ◽  
Addition Reaction ◽  
Epoxide Ring ◽  
Epoxide Ring Opening ◽  
Ring Opening Reaction ◽  
Nucleophilic Addition Reaction ◽  
Convergent Approach ◽  
Key Steps

The C1–C9 and C10–C24 segments of the 24-membered polyene macrolide macrolactin S were synthesized by routes involving an epoxide-ring-opening reaction, an Ohira–Bestmann alkyne formation, a chelation-controlled nucleophilic addition reaction, and a Still–Gennari olefination as key steps. A chiron approach , starting from readily available glucose diacetonide, was used to synthesize a key intermediate, and a convergent approach was adopted for the synthesis of the key C10–C24 fragment.

A protecting group free and scalable approach towards total synthesis of (−)-venlafaxine

RSC Advances ◽  
2014 ◽  
Vol 4 (28) ◽  
pp. 14468-14470 ◽  
Author(s):  
Subhash P. Chavan ◽  
Kailash P. Pawar ◽  
Sumanta Garai
Keyword(s):  
Total Synthesis ◽  
Ring Opening ◽  
Epoxide Ring ◽  
Protecting Group ◽  
Asymmetric Total Synthesis ◽  
Epoxide Ring Opening ◽  
Key Steps

A protecting group free asymmetric total synthesis of (−)-venlafaxine is reported. The strategy employs Sharpless epoxidation and regio-selective epoxide ring opening by an in situ generated Gilman reagent as key steps. This paper reports a 53% overall yield in 6 steps for total synthesis of (−)-venlafaxine.

First Total Synthesis of 3-Epi-calystegin B2

2011 ◽  
Vol 66 (3) ◽  
pp. 317-323
Author(s):  
René Csuk ◽  
Stefan Reißmann ◽  
Ralph Kluge ◽  
Dieter Ströhl ◽  
Claudia Korb
Keyword(s):  
Total Synthesis ◽  
Ring Opening ◽  
Tight Binding ◽  
Ring Closure ◽  
Hydroxyl Group ◽  
Target Compound ◽  
Metathesis Reaction ◽  
Ring Opening Reaction ◽  
Ultrasound Assisted ◽  
Key Steps

A straightforward chiral pool synthesis for a non-natural calystegin, 3-epi-B2, is described. Key steps of this synthesis include an ultrasound-assisted Zn-mediated tandem ring opening reaction followed by a Grubbs’ catalyst-mediated ring closure metathesis reaction. Compared to calystegin B2, the target compound is no longer an inhibitor for a β -glycosidase hence proving that an equatorial hydroxyl group at position C-3 is necessary for a tight binding of calystegins into the active site of β -glycosidases.

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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