ChemInform Abstract: A Convenient Stereoselective Synthesis of trans-4a,5,8,8a-Tetrahydro-2H-isoquinolin-1-ones via trans 3-Allylation of 4-Allyl-3,4-dihydropyridine-2-thiones and RCM as Key Steps.

ChemInform ◽  
2010 ◽  
Vol 41 (38) ◽  
pp. no-no
Author(s):  
Jacek G. Sosnicki ◽  
Lukasz Struk
Keyword(s):  
Stereoselective Synthesis ◽  
Key Steps

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.

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.

Total synthesis of haliclamide

2016 ◽  
Vol 14 (39) ◽  
pp. 9287-9293 ◽  
Author(s):  
Suraksha Gahalawat ◽  
Satyendra Kumar Pandey
Keyword(s):  
Total Synthesis ◽  
Stereoselective Synthesis ◽  
Steglich Esterification ◽  
Key Steps

A stereoselective synthesis of haliclamide has been developed. The synthesis includes MacMillan cross aldol, Mitsunobu inversion, Yamaguchi–Hirao alkylation, Steglich esterification and macrolactamization reactions and the Corey–Fuchs protocol as the key steps.

scholarly journals Synthesis of the Trans-Syn-Trans Perhydrobenzo[f]chromene Ring System

2021 ◽  
Author(s):  
Amjad Ayad Qatran AlKhdhairawi ◽  
Syahrul Imran ◽  
Nurhuda Manshoor ◽  
Geoffrey A. Cordell ◽  
Narendra Babu Shivanagere Nagojappa ◽  
...  
Keyword(s):  
Stereoselective Synthesis ◽  
Ring System ◽  
Unsaturated Ketone ◽  
Target Compound ◽  
Reductive Alkylation ◽  
Acid Catalyzed ◽  
Key Steps ◽  
Chromene Ring

<p>A stereoselective synthesis of the <i>trans</i>-<i>syn</i>-<i>trans </i>perhydrobenzo[<i>f</i>]chromene skeleton is presented. The target compound <b>3 </b>was achieved in six steps starting from the (<i>S</i>)-(+)-Wieland-Miescher ketone. Key steps include the sp<sup>2</sup> alkylation at the a-carbon of an unsaturated ketone, Birch-type reductive alkylation, and an acid-catalyzed cyclization. </p>

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.

Stereoselective Synthesis of Northern Fragment of Eribulin Mesylate from d-Mannose

Synthesis ◽  
2018 ◽  
Vol 50 (09) ◽  
pp. 1901-1906 ◽  
Author(s):  
Srivari Chandrasekhar ◽  
Vikram Gaddam ◽  
Lavanya Nadella ◽  
Genji Sukumar ◽  
Prathama Mainkar
Keyword(s):  
Stereoselective Synthesis ◽  
Eribulin Mesylate ◽  
Key Steps

Stereoselective synthesis of northern fragment of eribulin mesylate is reported by coupling of the C1–C13 fragment with the C28–C35 fragment. The key steps involved in this synthesis are butyllithium-facilitated coupling between sulfone and aldehyde, then Dess–Martin periodinane oxidation followed by samarium(II) iodide mediated desulfonylation.

A Stereoselective Synthesis of the ACE Inhibitor Trandolapril

Synlett ◽  
2019 ◽  
Vol 30 (07) ◽  
pp. 813-816 ◽  
Author(s):  
Slim Chiha ◽  
Matthias Spilles ◽  
Jörg-Martin Neudörfl ◽  
Hans-Günther Schmalz
Keyword(s):  
Acid Derivative ◽  
Building Block ◽  
Ace Inhibitor ◽  
Stereoselective Synthesis ◽  
Pyroglutamic Acid ◽  
Ring Closing Metathesis ◽  
12 Steps ◽  
Key Steps

A conceptually novel and stereoselective synthesis of the enantiopure octahydroindole building block and its conversion into the ACE inhibitor trandolapril was achieved. Key steps include the α-allylation of a protected l-pyroglutamic acid derivative, a highly diastereoselective Hosomi–Sakurai reaction and a Ru-catalyzed ring-closing metathesis of a 4,5-diallylated proline. This way, the synthesis of trandolapril was efficiently achieved in 25% overall yield (12 steps).

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.

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