Total Synthesis of Kingianin A

Lim, Hee Nam; Parker, Kathlyn A.

doi:10.1021/ol303388k

Cited by 56 publications

(29 citation statements)

References 23 publications

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“…Both (AE)kingianin A (1), a homochiral dimer, and (AE)-kingianin D (14), a heterochiral dimer, are the result of endo-selective formal Diels-Alder reactions occurring at the convex faces of both diene and dienophile. [36,37] Our results, in conjunction with previous biomimetic syntheses, [3,[10][11][12][13][14] demonstrate that (E,Z,Z,E)-tetraenes, and not their all-(Z) congeners, [32] are the likely biosynthetic precursors to bicyclo[4.2.0]octadiene natural products. The natural product (AE)-kingianin F (15) was similarly obtained by dimerization of the other bicyclo[4.2.0]octadiene diastereomer 12, followed by double oxidation and diamide formation.…”

supporting

confidence: 77%

“…Instead, we propose that nature uses a SET-mediated cycloaddition analogous to the approach described herein. [36,37] Our results, in conjunction with previous biomimetic syntheses, [3,[10][11][12][13][14] demonstrate that (E,Z,Z,E)-tetraenes, and not their all-(Z) congeners, [32] are the likely biosynthetic precursors to bicyclo[4.2.0]octadiene natural products. [38] Received: December 18, 2012 Published online: March 6, 2013 .…”

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confidence: 74%

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Total Synthesis of Kingianins A, D, and F

2013

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A synthesis fit for a king: The total synthesis of (±)‐kingianins A, D, and F has been achieved in ten steps. Key features include the gram‐scale synthesis and partial reduction of a conjugated tetrayne to a (Z,Z,Z,Z)‐tetraene, the domino 8π–6π electrocyclic ring closure of a (Z,Z,Z,Z)‐tetraene, and the radical‐cation‐catalyzed formal Diels–Alder dimerization of functionalized bicyclo[4.2.0]octadiene precursors.

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confidence: 77%

supporting

confidence: 74%

Total Synthesis of Kingianins A, D, and F

2013

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“…Parker et al 67 devised an imaginative radical cation Diels Alder approach that resulted in the macrocyclic intermediate (63) leading ultimately to kingianin A.…”

Section: Oxidative Generation Of Radical Cations In Pseudomacrocyclicmentioning

confidence: 99%

Treasures old and new: what we can learn regarding the macrocyclic problem from past and present efforts in natural product total synthesis

et al. 2020

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“…The compounds 141 and 142 were isolated in (13 %) and (16 %) as the major reaction products, respectively. The incidence of compound 141 [55] was momentous and through junction with the work of Parker, 138 provides an efficient synthesis of kingianin A 133. The construction of compound 142 can be clarified by anodic oxidation reaction with subsequent intramolecular etherification from the diastereoisomer 140, in which the nearby proximity of the endo-alcohol functionality and the cyclohexadiene core is enough ready to permit nucleophilic attack on the activated diene (Scheme 34).…”

Section: P E R S O N a L A C C O U N T T H E C H E M I C A L R E C O R Dmentioning

confidence: 99%

Electrochemically Induced Diels‐Alder Reaction: An Overview

Heravi

Zadsirjan

Kouhestanian

et al. 2019

The Chemical Record

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One of the most important name reactions in organic chemistry, is the Diels-Alder cycloaddition reaction. It is a chemical reaction between a conjugated diene and a substituted alkene, commonly termed the dienophile to construct a substituted cyclohexene derivative. It is the stereotypical example of a pericyclic reaction with a concerted mechanism. In synthesis, the use of electricity instead of stoichiometric amounts of oxidant or reducing agents is definitely appealing for economic, ecological and selective, reasons. In this review, we try to underscore the combination of the electrosynthesis with Diels-Alder cycloaddition reaction to establish of a powerful synthetic tool which may encourage synthetic organic chemists to use it in the future. Wiley Online LibraryScheme 6. A suggested mechanism of DÀ A reaction of electrogenerated quinones and dienes on the PTFE-fibers. Scheme 7. Electro-oxidation of Eugenol 77. P e r s o n a l A c c o u n t Wiley Online Library 286 Scheme 37. Anodic oxidation reaction of the 2-methoxy analogue 143 j and in situ trapping of the o-quinone heterodyne using enamine 144 a. Scheme 38. The synthesis of 145 e, 145 k-q using electro-oxidation pyrogallol derivatives with the enamine dienophiles. Scheme 48. The electrolysis of a 1 : 2 mixture of 3-buten-2-one ethylene acetal 183 a and cyclopentadiene 1 at 15 V for 0.2 F/mol using platinum electrodes in CH 2 C1 2 comprising LiC1O 4 /Bu 4 NC1O 4 as catalyst. Scheme 64. Regiospecific IEDDA reaction of enamine dienophile with o-azaquinone diene 232 ox , electrogenerated concurrently, to afford polyfunctionalized 1,4benzoxazine derivatives.

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Total Synthesis of Kingianin A

Cited by 56 publications

References 23 publications

Total Synthesis of Kingianins A, D, and F

Total Synthesis of Kingianins A, D, and F

Treasures old and new: what we can learn regarding the macrocyclic problem from past and present efforts in natural product total synthesis

Electrochemically Induced Diels‐Alder Reaction: An Overview

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