1998 Alfred Bader Award Lecture Tangents and targets: The synthetic highway from natural products to medicine

1999 ◽  
Vol 77 (2) ◽  
pp. 159-177 ◽  
Author(s):  
Alex G Fallis
Keyword(s):  
Natural Products ◽  
Building Blocks ◽  
Diels Alder ◽  
Synthetic Studies

Synthetic studies directed toward various classes of compounds including taxoids and enediyne systems are described. These investigations include tether-controlled imtramolecular Diels-Alder reactions, carbometallation routes to dienes and furans, the use of carbohydrate building blocks, pentadienyl indium reagents for tandem cycloadditions to steroid and triterpenoid skeletons, and the synthesis of taxamycins and revolveneynes and related cyclophanes.Key words: cycloaddition, taxoids, enediyne, cyclophanes, carbometallation.

ChemInform Abstract: Enzymatic Preparation of Optically Active Bicyclo(2.2.1)heptene Derivatives, Building Blocks for Terpenoid Natural Products. An Attractive Alternative to Enantioselective Diels-Alder Syntheses.

ChemInform ◽  
1989 ◽  
Vol 20 (34) ◽  
Author(s):  
J. VAN DER EYCKEN ◽  
M. VANDEWALLE ◽  
G. HEINEMANN ◽  
K. LAUMEN ◽  
M. P. SCHNEIDER ◽  
...  
Keyword(s):  
Natural Products ◽  
Building Blocks ◽  
Optically Active ◽  
Diels Alder ◽  
Attractive Alternative ◽  
Enzymatic Preparation

Competitive Intramolecular Diels - Alder Reactions of bis-α,β-Unsaturated Ester Derivatives of Enzymatically Derived and Enantiopure cis-1,2-Dihydrocatechols. Enantiodivergent Synthesis of Monochiral Bicyclo[2.2.2]oct-2-enes

2003 ◽  
Vol 56 (9) ◽  
pp. 861 ◽  
Author(s):  
Martin G. Banwell ◽  
Cai Chun ◽  
Alison J. Edwards ◽  
Markus M. Vögtle
Keyword(s):  
Natural Products ◽  
Single Crystal ◽  
Building Blocks ◽  
Diels Alder ◽  
Unsaturated Ester ◽  
Enantiomerically Pure ◽  
X Ray ◽  
Derivatives Of ◽  
Natural Products Synthesis

bis-Crotonate and related α,β-unsaturated ester derivatives of readily available and enantiomerically pure cis-1,2-dihydrocatechols engage, upon heating in refluxing toluene, in two competitive intramolecular Diels–Alder reactions to give varying mixtures of chromatographically separable and pseudo-enantiomeric bicyclo[2.2.2]oct-2-enes. Such adducts, many of which have been characterized by single-crystal X-ray analysis, are likely to serve as useful building blocks in natural products synthesis.

Latest Applications of the Diels-Alder Reaction in the Synthesis of Natural Products (2017-2020)

Synthesis ◽  
2021 ◽  
Author(s):  
Markus Kalesse ◽  
Aamer Saeed ◽  
Alexandru Sara ◽  
Um-e Farwa
Keyword(s):  
Natural Products ◽  
Natural Product ◽  
Building Blocks ◽  
Alder Reaction ◽  
Diels Alder ◽  
High Rank ◽  
Total Syntheses ◽  
Diels Alder Reaction ◽  
Natural Product Chemist

The Diels-Alder reaction has long established its high rank in the toolbox of any natural product chemist. The tremendous toleration of building blocks of various complexity and derivatization degree, as well as the enablement of furnishing six-membered rings with well-defined stereochemistry represents its main features and advantages. In recent years, many total syntheses of natural products relied at some point on the use of a [4+2]-cycloaddition step. Among classic approaches, several modifications of the Diels-Alder reaction, such as hetero-Diels-Alder reactions, dehydro-Diels-Alder reactions or domino-Diels-Alder reactions have been employed to extend the scope in the synthesis of natural products. Our review covers the application of the Diels-Alder reaction in natural product syntheses from 2017 to 2020, as well as selected methodologies which were inspired by, or could be used to access natural products.

Synthetic Studies of Biomimetic Diels-Alder Processes toward the Helicterin Family of Natural Products

2011 ◽  
Vol 51 (3-4) ◽  
pp. 378-390 ◽  
Author(s):  
Scott A. Snyder ◽  
Ferenc Kontes
Keyword(s):  
Natural Products ◽  
Diels Alder ◽  
Synthetic Studies

Biomimetic Synthesis of Hyperjapones F-I

2018 ◽  
Vol 71 (9) ◽  
pp. 649 ◽  
Author(s):  
Hiu C. Lam ◽  
Quang D. Phan ◽  
Christopher J. Sumby ◽  
Jonathan H. George
Keyword(s):  
Natural Products ◽  
Building Blocks ◽  
Diels Alder ◽  
Biomimetic Synthesis ◽  
Enantiomerically Pure ◽  
Biosynthetic Precursor ◽  
Hypericum Japonicum ◽  
Optical Rotations

Hyperjapones F–I are tetracyclic meroterpenoids recently isolated from Hypericum japonicum. All four of these natural products have been synthesised using oxidative, intermolecular hetero-Diels–Alder reactions to couple their common biosynthetic precursor, norflavesone, to the appropriate monoterpene building blocks: sabinene, β-pinene, and α-pinene. The synthesis of enantiomerically pure hyperjapones H and I and comparison of their optical rotations to those of the natural samples indicated that these meroterpenoids are probably biosynthesised as either racemic or scalemic mixtures.

Natural Products Biosynthesis Involving a Putative Diels-Alder Reaction

2016 ◽  
Vol 20 (22) ◽  
pp. 2421-2442 ◽  
Author(s):  
Kévin Cottet ◽  
Maria Kolympadi ◽  
Dean Markovic ◽  
Marie-Christine Lallemand
Keyword(s):  
Natural Products ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction

Chiral Sulfoxides as Building Blocks for Enantiopure 1,3-Diol Precursors in the Synthesis of Natural Products

2014 ◽  
Vol 10 (6) ◽  
pp. 885-902 ◽  
Author(s):  
Claude Bauder ◽  
Jean Martínez ◽  
Xavier Salom-Roig
Keyword(s):  
Natural Products ◽  
Building Blocks ◽  
Chiral Sulfoxides
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