scholarly journals Enantioselective total synthesis of decytospolide A and decytospolide B using an Achmatowicz reaction

2018 ◽  
Vol 16 (33) ◽  
pp. 5979-5986 ◽  
Author(s):  
Arun K. Ghosh ◽  
Hannah M. Simpson ◽  
Anne M. Veitschegger
Keyword(s):  
Total Synthesis ◽  
Transfer Hydrogenation ◽  
Enantioselective Total Synthesis ◽  
Key Steps ◽  
Enantioselective Syntheses

Enantioselective syntheses of decytospolides are described using an Achmatowicz rearrangement, transfer hydrogenation and Friedel–Crafts acylation as the key steps.

Enantioselective total synthesis of (S)-nakinadine B

RSC Advances ◽  
2016 ◽  
Vol 6 (31) ◽  
pp. 25913-25917 ◽  
Author(s):  
Yuvraj Garg ◽  
Satyendra Kumar Pandey
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Michael Addition ◽  
Marine Natural Product ◽  
Enantioselective Total Synthesis ◽  
Novel Approach ◽  
Key Steps

A novel approach for the synthesis of (S)-nakinadine B, a marine natural product is described. The synthesis utilizes the optimized combination of organocatalyzed Michael addition and aminoxylation reactions as key steps.

Enantioselective Total Synthesis of Ligraminol D and Ligraminol E

Synlett ◽  
2019 ◽  
Vol 30 (20) ◽  
pp. 2285-2289
Author(s):  
Baliram B. Mane ◽  
D. D. Kumbhar ◽  
Suresh B. Waghmode
Keyword(s):  
Total Synthesis ◽  
Mitsunobu Reaction ◽  
Bioactive Constituents ◽  
Ongoing Research ◽  
Total Syntheses ◽  
Enantioselective Total Synthesis ◽  
Key Steps

As a part of our ongoing research on the synthesis of bioactive constituents or molecules by using an organocatalytic approach, enantioselective total syntheses of ligraminol D and ligraminol E were achieved starting from a commercially available nonchiral aldehyde. Key steps in this synthesis were an asymmetric α-aminoxylation of an aldehyde and a Mitsunobu reaction.

Total Synthesis of (–)-Aristoquinoline via an Intramolecular Nitrilium Ion Cyclization

Synthesis ◽  
2021 ◽  
Author(s):  
Keith P. Reber ◽  
Priyansh D. Gujarati
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Building Block ◽  
Spectroscopic Properties ◽  
Ring System ◽  
Synthetic Route ◽  
Enantioselective Total Synthesis ◽  
Key Steps

AbstractThe enantioselective total synthesis of the alkaloid aristoquinoline has been achieved in seven steps and 26% overall yield. A new preparation of the useful synthetic building block (–)-α-terpinyl amine was also developed in order to avoid stoichiometric mercury reagents or azide-containing intermediates. Key steps in the optimized synthetic route include an intramolecular nitrilium ion cyclization to form the characteristic azabicyclo[3.3.1]nonane ring system and a dia­stereoselective reduction of the resulting imine mixture to afford the natural product. An isomer of aristoquinoline containing an exocyclic alkene was also obtained and found to exhibit unusual chromatographic and spectroscopic properties.

An enantioselective total synthesis of Sch-725674

2015 ◽  
Vol 13 (1) ◽  
pp. 234-240 ◽  
Author(s):  
Kota Ramakrishna ◽  
Krishna P. Kaliappan
Keyword(s):  
Total Synthesis ◽  
Metathesis Reaction ◽  
Stereoselective Reduction ◽  
Enantioselective Total Synthesis ◽  
Cross Metathesis ◽  
Yamaguchi Macrolactonization ◽  
Key Steps

An enantioselective total synthesis of Sch-725674 using dithiane alkylation, cross metathesis reaction, Yamaguchi macrolactonization and a substrate controlled stereoselective reduction as key steps is described.

First enantioselective total synthesis and configurational assignments of suberosenone and suberosanone as potential antitumor agents

2015 ◽  
Vol 51 (16) ◽  
pp. 3458-3461 ◽  
Author(s):  
Mohammad Kousara ◽  
Angélique Ferry ◽  
Franck Le Bideau ◽  
Kathalyn L. Serré ◽  
Isabelle Chataigner ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Antitumor Agents ◽  
Enantioselective Total Synthesis ◽  
Enantioselective Syntheses ◽  
Potential Antitumor

The first enantioselective syntheses of (1R)-suberosenone and (1R)-suberosanone are achieved, leading to revision of the AC of a natural (1S)-suberosanone.

scholarly journals Enantioselective Total Synthesis of (−)‐Finerenone Using Asymmetric Transfer Hydrogenation

2020 ◽  
Vol 132 (51) ◽  
pp. 23307-23311
Author(s):  
Andreas Lerchen ◽  
Narasimhulu Gandhamsetty ◽  
Elliot H. E. Farrar ◽  
Nils Winter ◽  
Johannes Platzek ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Transfer Hydrogenation ◽  
Asymmetric Transfer Hydrogenation ◽  
Enantioselective Total Synthesis

scholarly journals A New Organocatalytic Desymmetrization Reaction Enables the Enantioselective Total Synthesis of Madangamine E

2021 ◽  
Author(s):  
Shinya Shiomi ◽  
Benjamin D. A. Shennan ◽  
Ken Yamazaki ◽  
Ángel L. Fuentes de Arriba ◽  
Dhananjayan Vasu ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Density Functional ◽  
One Pot ◽  
Functional Theory ◽  
Bond Forming ◽  
Enantioselective Total Synthesis ◽  
Carbon Carbon Bond ◽  
Stereogenic Centers ◽  
Key Steps ◽  
Prochiral Ketone

The enantioselective total synthesis of madangamine E has been completed in 30 steps, enabled by a new catalytic and highly enantioselective desymmetrizing intramolecular Michael addition reaction of a prochiral ketone to a tethered β,β’-disubstituted nitroolefin. This key carbon–carbon bond forming reaction efficiently constructed a chiral bicyclic core in near-perfect enantio- and diastereo-selectivity, concurrently established three stereogenic centers, including a quaternary carbon stereocenter, and proved highly scalable. Furthermore, the pathway and origins of enantioselectivity in this catalytic cyclisation were probed using density functional theory (DFT) calculations, which revealed the crucial substrate/catalyst interactions in the enantio-determining step. Following construction of the bicyclic core, the total synthesis of madangamine E could be completed, with key steps including a mild one-pot oxidation-lactamisation, a two-step Z-selective olefination of a sterically hindered ketone, and ring-closing metatheses to install the two macrocyclic rings.

Sign in / Sign up

Export Citation Format

Share Document