A Modular Approach to Oxoindolizino Quinolines: Efficient Synthesis of Mappicine Ketone (Nothapodytine B)

Raolji, Gajendra B.; Garçon, Stéphanie; Greene, Andrew E.; Kanazawa, Alice

doi:10.1002/anie.200352094

Cited by 33 publications

(8 citation statements)

References 25 publications

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“…Our group demonstrated the versatility of the method through the synthesis of the angiotensin converting enzyme inhibitor (À)-A58365A (52), (AE)-ipalbidine (53), b-carbolinone 54 and a variety of other novel indolizidine-based compounds. 20 The use of 50 as a key intermediate in total synthesis has also been demonstrated by Greene and coworkers 21 in a recent synthesis of the antiviral agent mappicine ketone, one of the alkaloids isolated together with campothecin from the Indian plant Nothapodytes foetida.…”

Section: Alkaloid Synthesis Using Isomu¨nchnones As Key Intermediatesmentioning

confidence: 88%

Domino reactions of rhodium(ii) carbenoids for alkaloid synthesis

Padwa¹

2009

Chem. Soc. Rev.

396

104

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In this tutorial review, the rhodium(II)-catalyzed domino reactions of alpha-diazo carbonyl compounds are summarized. The article will emphasize some of the more recent synthetic applications of the rhodium carbenoid cyclization/cycloaddition domino cascade for alkaloid synthesis. The many structurally diverse and highly successful examples of both oxa and azapolycyclic ring formation cited in this tutorial review clearly demonstrate that the domino cyclization/cycloaddition cascade of metallo carbenoids has evolved as an important strategy for the synthesis of nitrogen containing natural products.

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Section: Alkaloid Synthesis Using Isomu¨nchnones As Key Intermediatesmentioning

confidence: 88%

Domino reactions of rhodium(ii) carbenoids for alkaloid synthesis

Padwa¹

2009

Chem. Soc. Rev.

396

104

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“…71 The synthesis of 144 began with formation of the known cycloadduct 139a (R 1 = H; R 2 = CO 2 Me) by cycloaddition of the isomünchnone dipole derived from diazo sulfone 138 with methyl acrylate (Scheme 27). [67][68][69][70] This multistep sequence proceeded smoothly and in high yield when catalyzed by rhodium(II) acetate.…”

Section: Mappicine Ketonementioning

confidence: 99%

Use of nitrogen and oxygen dipole ylides for alkaloid synthesis

Padwa¹

2018

Arkivoc

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As highlighted in this mini review, a growing area of interest in organic synthesis involves the use of substituted azomethine and carbonyl ylides as 1,3-dipoles for the preparation of alkaloidal natural products. Cascade reactions proceeding by an intramolecular 1,3-dipolar cycloaddition of nitrogen and oxygen dipole ylides are of particular interest to the synthetic organic community because of the increase in molecular complexity involved and the high isolated yields.

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“…They show a diversity of bioactive properties such as antitumor, antimicrobial, anti-inflammatory, cardiotonic, antiviral, and antimalarial activity . These scaffolds are also important intermediates in many organic transformations . A series of methods have been developed for the synthesis of 1,6-annulated 2-pyridones and 2,3-annulated 4-pyrimidinones such as intramolecular nucleophilic substitution, radical cyclization, intramolecular alkenylation, and intramolecular Heck reaction.…”

mentioning

confidence: 99%

A Gold(I)-Catalyzed Hydroamination/Cycloisomerization Cascade: Concise Synthesis of (±)-seco-Antofine and (±)-Septicine

Tian

Song

et al. 2020

Org. Lett.

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A concise and flexible procedure for the synthesis of highly functionalized N-heterocyclic 1,6-annulated 2-pyridones and 2,3-annulated 4-pyrimidinones has been elaborated through a gold-catalyzed tandem hydroamination/cycloisomerization cascade. This novel and highly efficient method allows the rapid construction of these diverse N-heterocyclic scaffolds starting from readily available building blocks, and shows a wide scope and good functional group tolerance. The total synthesis of (±)-seco-antofine and (±)-septicine were realized employing this strategy.

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A Modular Approach to Oxoindolizino Quinolines: Efficient Synthesis of Mappicine Ketone (Nothapodytine B)

Cited by 33 publications

References 25 publications

Domino reactions of rhodium(ii) carbenoids for alkaloid synthesis

Domino reactions of rhodium(ii) carbenoids for alkaloid synthesis

Use of nitrogen and oxygen dipole ylides for alkaloid synthesis

A Gold(I)-Catalyzed Hydroamination/Cycloisomerization Cascade: Concise Synthesis of (±)-seco-Antofine and (±)-Septicine

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