Mukaiyama–Michael Reactions with Acrolein and Methacrolein: A Catalytic Enantioselective Synthesis of the C17–C28 Fragment of Pectenotoxins

Kemppainen, Eeva K.; Sahoo, Gokarneswar; Valkonen, Arto; Pihko, Petri M.

doi:10.1021/ol203486p

Cited by 64 publications

(43 citation statements)

References 47 publications

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“…The combined organic extracts were washed with brine (30 mL) and dried with Na 2 SO 4 . The solvent was removed in vacuo, and the residue was purified by distillation (0.1 mbar, 83 °C) to furnish the title compound (5.63 g, 98 %, ref . 94 %) as a colorless liquid.…”

Section: Methodsmentioning

confidence: 99%

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Establishing Consensus Stereostructures for the Naphthoquinonopyrano‐γ‐lactone Natural Products (–)‐Arizonin B1 and (–)‐Arizonin C1 by Total Syntheses. Diastereocontrol of Oxa‐Pictet–Spengler Cyclizations by Protective‐Group Optimization

Neumeyer

Brückner

2017

Eur J Org Chem

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Previous total syntheses of arizonin C1 (4) led to opposite assignments of its absolute configuration. Here, we report the fourth total synthesis thereof. In addition, we disclose the first total synthesis of arizonin B1 (3) proceeding differently than via arizonin C1. The stereocenters of the two targets stemmed from an asymmetric dihydroxylation and an ensuing oxa‐Pictet–Spengler cyclization. Their configurations were in line with Fernandes' assignments. Protective‐group variation in the substrate modulated the diastereoselectivity of the Pictet–Spengler cyclization between 77:23 in favor of a trans disubstitution at C‐3a vs. C‐5 – used for preparing the natural (–)‐arizonins C1 and B1 – and 100:0 in favor of a cis disubstitution – exploited for synthesizing the unnatural (+)‐5‐epi‐arizonins C1 and B1. All naphthalenes of the present study were derived from the (benzyloxy)methoxynaphthalenediol 19. It resulted from a Diels–Alder reaction of the aryne 17a with the siloxyfuran 18a.

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Section: Methodsmentioning

confidence: 99%

“…), H 2 O 2 (30 % in H 2 O, 2.0 equiv. ), Na 2 SO 4 , room temp., 16 h; 59 % (ref . 58 %); (f) i Pr 3 SiOTf (1.2 equiv.…”

Section: Introductionmentioning

confidence: 99%

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Establishing Consensus Stereostructures for the Naphthoquinonopyrano‐γ‐lactone Natural Products (–)‐Arizonin B1 and (–)‐Arizonin C1 by Total Syntheses. Diastereocontrol of Oxa‐Pictet–Spengler Cyclizations by Protective‐Group Optimization

Neumeyer

Brückner

2017

Eur J Org Chem

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“…Our planned synthesis began with a known aldehyde 4 prepared from corresponding olefin through ozonolysis, [22][23] which was subjected to aldol condensation with 2-furanone 24 followed by exposure to triethylamine/acetic anhydride produced a mixture of E/Zisomers of 3 (~1:3 ratio). 25 Allylic oxidation of exocyclic olefin present in 3 using selenium dioxide in 1,4-dioxane furnished two alcohols 5 and 6 in 69% yield.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of revised structure of klaivanolide (acetylmelodorinol)

Raut¹,

Wagh²,

Reddy³

2015

Arkivoc

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Klaivanolide (acetylmelodorinol) is an anti-leishmanial/anti-trypanosomal agent isolated from Uvaria klaineana and the structure was originally assigned as a 7-membered lactone with extended conjugation and S-configuration at the lactone junction. Very recently, the structure of klaivanolide was revised as previously known compound acetylmelodorinol. Now, we have synthesized the revised structure in racemic form using a short route.

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“…[95] In addition, another stereocenter must be generated at C27. [95] In addition, another stereocenter must be generated at C27.…”

Section: Organocatalytic Mukaiyama-michael Reactions 41 Imidazolidimentioning

confidence: 99%

Development and Application of Asymmetric Organocatalytic Mukaiyama and Vinylogous Mukaiyama‐Type Reactions

Frías

Cieślik

Fraile

et al. 2018

Chemistry A European J

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Organocatalysis is a growing area that is benefiting from advances in many fields. Its implementation has begun in areas such as supramolecular chemistry, organic chemistry and natural product synthesis. While a considerable number of important publications in the field of organocatalytic Mukaiyama-type additions have been reported, they are yet to be fully covered in a review. Therefore, we would like to highlight the applications of various kinds of organocatalysts in Mukaiyama-type reactions, while also including the vinylogous Mukaiyama variation. Herein we describe and discuss the development and current state of the art of the organocatalytic Mukaiyama reaction, vinylogous Mukaiyama and related reactions.

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Mukaiyama–Michael Reactions with Acrolein and Methacrolein: A Catalytic Enantioselective Synthesis of the C17–C28 Fragment of Pectenotoxins

Cited by 64 publications

References 47 publications

Establishing Consensus Stereostructures for the Naphthoquinonopyrano‐γ‐lactone Natural Products (–)‐Arizonin B1 and (–)‐Arizonin C1 by Total Syntheses. Diastereocontrol of Oxa‐Pictet–Spengler Cyclizations by Protective‐Group Optimization

Establishing Consensus Stereostructures for the Naphthoquinonopyrano‐γ‐lactone Natural Products (–)‐Arizonin B1 and (–)‐Arizonin C1 by Total Syntheses. Diastereocontrol of Oxa‐Pictet–Spengler Cyclizations by Protective‐Group Optimization

Synthesis of revised structure of klaivanolide (acetylmelodorinol)

Development and Application of Asymmetric Organocatalytic Mukaiyama and Vinylogous Mukaiyama‐Type Reactions

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