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

1989 ◽  
Vol 0 (5) ◽  
pp. 306-308 ◽  
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

Synthesis of Optically Active Cyclopenta[c]pyran-4-carboxylic Acid Derivatives, Building Blocks for Iridoids. An Attractive Alternative to Asymmetric de Mayo Reaction

1989 ◽  
Vol 18 (11) ◽  
pp. 1925-1928 ◽  
Author(s):  
Masayuki Sato ◽  
Kazuhisa Takayama ◽  
Keiko Sekiguchi ◽  
Yoshito Abe ◽  
Toshio Furuya ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Building Blocks ◽  
Optically Active ◽  
Attractive Alternative

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.

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.

Catalytic Asymmetric Osmium-Free Dihydroxylation of Alkenes

Synthesis ◽  
2020 ◽  
Author(s):  
Chuan Wang ◽  
Shixia Su
Keyword(s):  
Natural Products ◽  
Organic Synthesis ◽  
Phase Transfer ◽  
Building Blocks ◽  
Short Review ◽  
Optically Active ◽  
Asymmetric Dihydroxylation ◽  
A Subunit ◽  
Vicinal Diols ◽  
Catalytic Asymmetric

AbstractAsymmetric dihydroxylation of alkenes is one of the cornerstone reactions in organic synthesis, providing a direct entry to optically active vicinal diols, which are not only a subunit in natural products but also versatile building blocks. In recent years, considerable progress in catalytic asymmetric osmium-free dihydroxylation has been achieved. This short review presents a concise summary of the reported methods of catalytic asymmetric osmium-free dihydroxylation.1 Introduction2 Iron-Catalyzed Asymmetric syn-Dihydroxylation of Alkenes3 Manganese-Catalyzed Asymmetric syn-Dihydroxylation of Alkenes4 Palladium/Gold Bimetallic Nanocluster-Catalyzed Asymmetric syn-Dihydroxylation of Alkenes5 Enzyme-Catalyzed Asymmetric anti-Dihydroxylation of Alkenes6 Amine-Catalyzed Asymmetric Formal anti-Dihydroxylation of Enals7 Diselenide-Catalyzed anti-Dihydroxylation of Alkenes8 Molybdenum-Catalyzed Asymmetric anti-Dihydroxylation of Allylic­ Alcohols9 Phase-Transfer-Catalyzed Asymmetric Dihydroxylation of α-Aryl Acrylates10 Conclusion

The stereoselective formation of highly substituted CF3-dihydropyrans as versatile building blocks

2015 ◽  
Vol 51 (71) ◽  
pp. 13666-13669 ◽  
Author(s):  
Bjarke S. Donslund ◽  
Alicia Monleón ◽  
Jesper Larsen ◽  
Lise Ibsen ◽  
Karl Anker Jørgensen
Keyword(s):  
Building Blocks ◽  
Alder Reaction ◽  
Optically Active ◽  
Diels Alder ◽  
Inverse Electron Demand ◽  
Diels Alder Reaction ◽  
Formal Inverse ◽  
Electron Demand

The dienamine-mediated formal inverse electron demand hetero Diels–Alder reaction providing optically active 5-bromo-6-(trifluoromethyl)-3,4-dihydro-2H-pyrans is disclosed along with interesting transformations, affording a large variety of fully substituted dihydropyrans.

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