Enantioselective isoquinuclidine synthesis via sequential Diels–Alder/visible-light photoredox C–C bond cleavage: a formal synthesis of the indole alkaloid catharanthine

2018 ◽  
Vol 5 (20) ◽  
pp. 2934-2939 ◽  
Author(s):  
Simon J. Kim ◽  
Robert A. Batey
Keyword(s):  
Visible Light ◽  
Bond Cleavage ◽  
Indole Alkaloid ◽  
Alder Reaction ◽  
Diels Alder ◽  
Formal Synthesis ◽  
Diels Alder Reaction ◽  
Alkaloid Synthesis

An enantioselective formation of isoquinuclidines useful for alkaloid synthesis is achieved through an organocatalyzed Diels–Alder reaction of dihydropyridines with acrolein and a subsequent photoredox catalyzed oxidative deformylation reaction.

Enantioselective Synthesis of Cyclic Ethers via Hetero Diels-Alder Reaction. Formal Synthesis of (+)- and (-)-Laurecin

Synlett ◽  
1996 ◽  
Vol 1996 (10) ◽  
pp. 983-984 ◽  
Author(s):  
M. Teresa Mujica ◽  
María M. Afonso ◽  
Antonio Galindo ◽  
J. Antonio Palenzuela
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Enantioselective Synthesis ◽  
Cyclic Ethers ◽  
Formal Synthesis ◽  
Diels Alder Reaction

scholarly journals Synthesis of a Biomimetic Tetracyclic Precursor of Aspochalasins Allowing a Formal Synthesis of Trichoderone A

2021 ◽  
Author(s):  
Oscar Gayraud ◽  
Benjamin Laroche ◽  
Nicolas Casaretto ◽  
Bastien Nay
Keyword(s):  
Total Synthesis ◽  
Claisen Rearrangement ◽  
Alder Reaction ◽  
Diels Alder ◽  
Two Phase ◽  
Formal Synthesis ◽  
Diels Alder Reaction ◽  
Oxidative Transformations ◽  
High Degree

Aspochalasins are leucine-derived cytochalasins. Their complexity is often associated to a high degree of biosynthetic oxidative transformations that could inspire a two-phase strategy in total synthesis. In that context, we describe the synthesis of a putative biomimetic tetracyclic intermediate. The key constructive steps are an intramolecular Diels-Alder reaction to install the characteristic isoindolone core of cytochalasins, whose branched precursor was obtained from a stereoselective Ireland-Claisen rearrangement made on a highly unsaturated substrate. This work also constitutes a formal synthesis of trichoderone A.

Diels–Alder approach to (±)-longifolene: A formal synthesis

1992 ◽  
Vol 70 (5) ◽  
pp. 1375-1384 ◽  
Author(s):  
Tse-Lok Ho ◽  
Wen-Lung Yeh ◽  
John Yule ◽  
Hsing-Jang Liu
Keyword(s):  
Maleic Anhydride ◽  
Ring Expansion ◽  
Alder Reaction ◽  
Diels Alder ◽  
Formal Synthesis ◽  
Racemic Form ◽  
Diels Alder Reaction ◽  
Key Steps

A formal synthesis of longifolene in racemic form is concluded starting from the Diels–Alder reaction of 6,6-di-methylfulvene and maleic anhydride. Key steps are cyclodehydration, conjugate methylation, and ring expansion.

Alkaloid synthesis by the intramolecular imino Diels-Alder reaction. .delta.-Coniceine and tylophorine

1979 ◽  
Vol 101 (17) ◽  
pp. 5073-5074 ◽  
Author(s):  
Steven M. Weinreb ◽  
Nazir A. Khatri ◽  
Jayant Shringarpure
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Alkaloid Synthesis
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