Recent applications of the hetero Diels–Alder reaction in the total synthesis of natural products

Heravi, Majid M.; Ahmadi, Tahereh; Ghavidel, Mahdieh; Heidari, Bahareh; Hamidi, Hoda

doi:10.1039/c5ra17488k

Cited by 133 publications

(50 citation statements)

References 558 publications

(616 reference statements)

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“…32 We are interested in the asymmetric synthesis, [35][36][37][38][39][40][41][42][43] and applications of named reactions in the total synthesis of natural products which usually use asymmetric synthesis in one or more steps in their multi-step synthesis. [44][45][46][47][48] Due to the increasing number of articles published concerning asymmetric 1,4-addition reactions, catalyzed by Rh-complexes, we were prompted to update the invaluable review by Hayashi et al in 2003. 32 Herein we highlight the recent advances in Rhcomplex asymmetric catalyzed 1,4-addition reactions from 2003 to date.…”

Section: Introductionmentioning

confidence: 98%

Rh-catalyzed asymmetric 1,4-addition reactions to α,β-unsaturated carbonyl and related compounds: an update

Heravi

Dehghani

Zadsirjan

2016

Tetrahedron: Asymmetry

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109

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Rh-catalyzed asymmetric 1,4-addition reactions to a,b-unsaturated carbonyl and related compounds: an update Available online xxxx Dedicated to my son, OMID on the occasion of his 35th birthday. a b s t r a c tThe Rh-catalyzed asymmetric 1,4-addition of organometallic reagents to an appropriate receptor has been a growing area of research over the last decade. The receptors for such a 1,4-addition reaction are chiefly a,b-unsaturated ketones, esters, amides, enones, nitroalkenes, and occasionally phosphonates etc. This reaction in the presence of chiral rhodium complexes introduce the aryl and alkenyl groups at the b-position of the above electron poor olefins, enantioselectively. Chiral Rh complexes similar to other transition metals can be added to some electron poor olefins, in turn making them viable to attack by various organometallic reagents for highly enantioselective C-C bond formation. The Rh-catalyzed asymmetric 1,4-addition of organometallic reagents to electron poor olefins has been reviewed in 2003. Due to the importance of the asymmetric C-C bond formation via 1,4-conjugate addition reactions and the number of such reactions catalyzed by Rh-complexes, in this review we highlight the recent advances in Rh-complex asymmetric catalyzed 1,4-addition reactions since 2003.

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Section: Introductionmentioning

confidence: 98%

Rh-catalyzed asymmetric 1,4-addition reactions to α,β-unsaturated carbonyl and related compounds: an update

Heravi

Dehghani

Zadsirjan

2016

Tetrahedron: Asymmetry

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109

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“…In recent years, our research group showed interest and focused on the applications of name reactions in the total synthesis of natural products . Among them, in 2012 we published a report, covering the applications of SMCR in the total synthesis of natural products in Tetrahedron, which has seemingly attracted much attention of synthetic organic chemists due to numerous citations it has gained till date.…”

Section: Introductionmentioning

confidence: 99%

Current Applications of Suzuki–Miyaura Coupling Reaction in The Total Synthesis of Natural Products: An update

Koshvandi

Heravi

Momeni

2018

Applied Organom Chemis

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168

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Suzuki‐Miyaura Coupling Reaction (SMCR) has been extensively used in the total synthesis of natural products. We underscored these achievements in a report published in Tetrahedron up to 2012. Since then, there has been tremendous growth in this field and numerous articles have been published after 2012. In this review, we tried to go insight and highlight the current developments in the applications of SMCR as a key and strategic step (steps) in the total synthesis of biologically active natural products accomplished and reported from 2012 till date.

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“…Hetero-Diels–Alder reactions are considered to be a powerful methodology widely explored for the synthesis of six-membered heterocycles [1–2] with numerous applications for the construction of complex molecules including naturally occurring products [3–4], drugs [5–6], agrochemicals [7], etc. In addition, asymmetric hetero-Diels–Alder reactions are of current interest [8–10].…”

Section: Introductionmentioning

confidence: 99%

First thia-Diels–Alder reactions of thiochalcones with 1,4-quinones

Mlostoń

Urbaniak

et al. 2018

Beilstein J. Org. Chem.

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Aryl and hetaryl thiochalcones react smoothly with 1,4-quinones in THF solution at 60 °C yielding the corresponding fused 4H-thiopyrans after spontaneous dehydrogenation of the initially formed [4 + 2] cycloadducts. In general, the yields of the isolated products were high. With 5-chloro-10-hydroxy-1,4-anthraquinone, the thia-Diels–Alder reaction occurred with complete regioselectivity. In the case of the reaction of vitamin K3 (menadione) with diphenylthiochalcone, the initial cycloadduct was isolated in 37% yield.

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Recent applications of the hetero Diels–Alder reaction in the total synthesis of natural products

Abstract: The synthetic utility and potential power of the Diels–Alder (D–A) reaction in organic chemistry is evident.

Cited by 133 publications

References 558 publications

Rh-catalyzed asymmetric 1,4-addition reactions to α,β-unsaturated carbonyl and related compounds: an update

Rh-catalyzed asymmetric 1,4-addition reactions to α,β-unsaturated carbonyl and related compounds: an update

Current Applications of Suzuki–Miyaura Coupling Reaction in The Total Synthesis of Natural Products: An update

First thia-Diels–Alder reactions of thiochalcones with 1,4-quinones

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