Synthesis of the Natural Product Building Block 5-(3-Bromophenyl)-4-hydroxy-5-methylhexan-2-one and its Chiral Characterization by Using Chiroptical Spectroscopy

ChemPhysChem ◽  
2013 ◽  
Vol 14 (14) ◽  
pp. 3255-3262 ◽  
Author(s):  
Ewoud De Gussem ◽  
Jelle Cornelus ◽  
Sam Pieters ◽  
Dries Van den Bossche ◽  
Johan Van der Eycken ◽  
...  
Keyword(s):  
Natural Product ◽  
Building Block ◽  
Chiroptical Spectroscopy

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.

ChemInform Abstract: Hagemann′s Ester: A Timeless Building Block for Natural Product Synthesis

ChemInform ◽  
2010 ◽  
Vol 41 (29) ◽  
pp. no-no
Author(s):  
Gian Piero Pollini ◽  
Simonetta Benetti ◽  
Carmela De Risi ◽  
Vinicio Zanirato
Keyword(s):  
Natural Product ◽  
Building Block ◽  
Natural Product Synthesis

Chemo-enzymatic synthesis of the C15–C23 unit of Leptomycin B

2002 ◽  
Vol 80 (6) ◽  
pp. 571-576 ◽  
Author(s):  
Michael Scheck ◽  
Herbert Waldmann
Keyword(s):  
Asymmetric Synthesis ◽  
Natural Product ◽  
Building Block ◽  
Enzymatic Synthesis ◽  
Aldol Reaction ◽  
Natural Product Synthesis ◽  
Leptomycin B ◽  
Enzymatic Transformation

The asymmetric synthesis of the C15–C23 unit of Leptomycin B (LMB) is described. All four stereocenters of the C15–C23 unit were prepared from one building block exhibiting only one stereocenter. This building block was synthesized via either an enzymatic transformation or starting from a chiral reagent.Key words: Leptomycin, natural product synthesis, enzymatic transformation, Aldol reaction, Pseudomonas fluorescence lipase (PFL).

Hagemann's ester: a timeless building block for natural product synthesis

Tetrahedron ◽  
2010 ◽  
Vol 66 (15) ◽  
pp. 2775-2802 ◽  
Author(s):  
Gian Piero Pollini ◽  
Simonetta Benetti ◽  
Carmela De Risi ◽  
Vinicio Zanirato
Keyword(s):  
Natural Product ◽  
Building Block ◽  
Natural Product Synthesis

Bifunctional oxindole-chromone 4C building block directed asymmetric synthesis of bispirocyclic hexahydroxanthones featuring five contiguous stereocenters and two side-by-side oxindoles

2019 ◽  
Vol 6 (10) ◽  
pp. 1603-1607 ◽  
Author(s):  
Xiong-Li Liu ◽  
Yi Gong ◽  
Shuang Chen ◽  
Xiong Zuo ◽  
Zhen Yao ◽  
...  
Keyword(s):  
Small Molecules ◽  
Asymmetric Synthesis ◽  
Natural Product ◽  
Building Block ◽  
Three Dimensional ◽  
Optically Active ◽  
High Demand ◽  
Dimensional Complexity

Optically active small molecules based on privileged natural product frameworks and rich in three-dimensional complexity are in high demand.

Sign in / Sign up

Export Citation Format

Share Document