scholarly journals Enantioselective Catalysis on the Solid Phase: Synthesis of Natural Product-Derived Tetrahydropyrans Employing the Enantioselective Oxa-Diels–Alder Reaction

2006 ◽  
Vol 348 (12-13) ◽  
pp. 1511-1515 ◽  
Author(s):  
Miguel A. Sanz ◽  
Tobias Voigt ◽  
Herbert Waldmann
Keyword(s):  
Natural Product ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Alder Reaction ◽  
Diels Alder ◽  
Enantioselective Catalysis ◽  
Phase Synthesis ◽  
Diels Alder Reaction

Solid-Phase Organic Synthesis of Dexoxadrol Analogues

2013 ◽  
Vol 66 (1) ◽  
pp. 93 ◽  
Author(s):  
Michael Sax ◽  
Bernhard Wünsch
Keyword(s):  
Solid Phase ◽  
Alder Reaction ◽  
Solid Support ◽  
Diels Alder ◽  
Piperidine Ring ◽  
Phase Synthesis ◽  
Diels Alder Reaction ◽  
Conjugate Reduction ◽  
Solid Phase Organic Synthesis ◽  
Danishefsky's Diene

A solid-phase synthesis of dexoxadrol analogues like-13 and unlike-13 bearing an oxo group in the 4-position of the piperidine ring has been developed using aminomethyl substituted polystyrene resin as solid support. The synthesis comprises a hetero-Diels–Alder reaction of imine 7b with Danishefsky’s diene 8 in the presence of the Lewis acid Yb(OTf)3 and a conjugate reduction of the double bond of 9b with LiBHEt3 and BF3. The cleavage of the product from the solid support was performed with 1-chloroethyl chloroformate. All transformations on the solid support and additionally the cleavage reaction had to be compatible with the large and acid labile acetalic 1,3-dioxolane moiety in 2-position of the piperidine ring. The oxodexoxadrol derivative 12 was obtained in an overall yield of 17 %.

Asymmetric Synthesis of 3,3′-Piperidinoyl Spirooxindoles and Discovery of Stereospecific Cycloadducts as Novel Hedgehog Pathway Modulators

Synthesis ◽  
2020 ◽  
Vol 52 (21) ◽  
pp. 3140-3152
Author(s):  
Kamal Kumar ◽  
Mohammad Rehan ◽  
Jana Flegel ◽  
Franziska Heitkamp ◽  
Jorgelina L. Pergomet ◽  
...  
Keyword(s):  
Transition Metal ◽  
Small Molecules ◽  
Asymmetric Synthesis ◽  
Natural Product ◽  
Transition Metal Complexes ◽  
Alder Reaction ◽  
Diels Alder ◽  
Hedgehog Pathway ◽  
Diels Alder Reaction ◽  
Efficient Access

An enantioselective hetero-Diels–Alder reaction of alkylidene­ oxindoles and 2-aza-3-silyloxy-1,3-butadienes, catalyzed by divalent transition metal complexes with N,N′-dioxide ligands offered an efficient access to natural-product-based 3,3′-piperidinoyl spiroox­indole class of small molecules. exo-Cycloadducts formed via stereospecific cycloaddition with Z-olefin displayed potent activity in modulation of hedgehog pathway.

scholarly journals The Total Synthesis of (–)-Scabrolide a

2020 ◽  
Author(s):  
Nicholas Hafeman ◽  
Steven A. Loskot ◽  
Chris Reimann ◽  
Beau P. Pritchett ◽  
Scott C. Virgil ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction

The first total synthesis of the norcembranoid diterpenoid scabrolide A is disclosed. The route begins with the synthesis of two chiral pool-derived fragments, which undergo a convergent coupling to expediently introduce all 19 carbon atoms of the natural product. An intramolecular Diels–Alder reaction and an enone-olefin cycloaddition/fragmentation sequence are then employed to construct the fused [5–6–7] linear carbocyclic core of the molecule and to complete the total synthesis.

Advances in Solution- and Solid-Phase Synthesis toward the Generation of Natural Product-like Libraries

2009 ◽  
Vol 109 (5) ◽  
pp. 1999-2060 ◽  
Author(s):  
Jyoti P. Nandy ◽  
Michael Prakesch ◽  
Shahriar Khadem ◽  
P. Thirupathi Reddy ◽  
Utpal Sharma ◽  
...  
Keyword(s):  
Natural Product ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis
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