Domino Reaction of 2,3‐Epoxy‐1‐alcohols and PIFA in the Presence of H<sub>2</sub>O and the Concise Synthesis of (+)‐Tanikolide

Kita, Yasuyuki; Matsuda, Satoshi; Fujii, Eri; Horai, Mai; Hata, Katsuhiko; Fujioka, Hiromichi

doi:10.1002/anie.200501686

Cited by 41 publications

(21 citation statements)

References 34 publications

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“…A number of other reports have also appeared in the last two years, including the molybdenum carbonyl mediated tandem allenic Pauson-Khand reaction [76] in the presence of CO-the highly enantio-and diastereoselective one-pot synthesis [77] of acyclic epoxy alcohols and allylic epoxy alcohols, the domino ring-opening/rearrangement reaction [78] of 2,3-epoxy-1-alcohols and PIFA(phenyliodine(III) bis(trifluoroacetate)), the tandem [4+2]/1,3-dipolar [3+2] cycloaddition of oxadiazoles [79] that allowed direct access to the pentacyclic aspidosperma skeleton in a reaction cascade forming four new C-C bonds and three new rings, and a catalytic asymmetric three-component 1,4-addition/aldol reaction in the enantioselective synthesis [80] of the spirocyclic moiety of Vannusal A. All these will not be detailed here due to space limitation.…”

Section: Tandem Reactionsmentioning

confidence: 96%

A new era for organic synthesis—highlights of the recent progress

Yikang

2007

Front. Chem. China

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The major progress in organic synthesis since 2005 is briefly surveyed in two parts. The first part deals with some of the most impressive advances in the synthetic methodology, which includes: (1) metal-mediated synthetic reactions, with an emphasis on the olefin metathesis and gold-mediated reactions; (2) free radical-based organic synthesis; (3) synthetic transformations performed in a "one-pot" manner involving either tandem reactions or multicomponent reactions; (4) asymmetric reactions catalyzed by metal and organo-catalysts. The major advances in total synthesis of some complex natural products with significant biological activities are presented in the second part, with detailed illustrations of ten selected molecules, including dragmacidin F, abyssomicin C, 11-acetoxy-4-deoxyasbestinin D, pentacycloanammoxic acid, UCS1025A, (−)-merrilactone A, nigellamine A 2 , (+)-saxitoxin, and Tamiflu (an artificially designed natural product-like molecule). An array of complicated structures of the natural products synthesized over the last two years is also listed to serve as a convenient lead to the original literature for the prospective interested readers.Keywords organic synthesis, metal-mediated synthetic reaction, free radical reaction, "in one pot" reaction, asymmetric reaction, total synthesis of natural products Organic reactions are of central importance to organic synthetic methodology and underlie all types of organic A new era for organic synthesis-highlights of the recent progress

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Section: Tandem Reactionsmentioning

confidence: 96%

A new era for organic synthesis—highlights of the recent progress

Yikang

2007

Front. Chem. China

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“…[Bis(trifluoroacetoxy)iodo]benzene can initiate the rearrangement of a 2,3-epoxy-1-alcohols of type 131 into lactols 132 as shown in Scheme 37 [30,31]. With R ¼ H, the reaction leads to lactol 133.…”

Section: Other Rearrangementsmentioning

confidence: 96%

Rearrangements Induced by Hypervalent Iodine

Maertens

Canesi

2015

Topics in Current Chemistry

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This chapter describes advances in hypervalent iodine(III)-induced rearrangements reported between 2004 and 2015, beginning with Hofmann-type rearrangements and aliphatic aryl transpositions. In both reactions the iodine(III) reagent may be off-the-shelf or catalytically generated in situ. A number of stereoselective transformations are discussed, followed by transpositions triggered through phenol dearomatization, including Wagner-Meerwein-type rearrangements, Prins-pinacol transpositions, and a tandem polycylization-pinacol process. Other rearrangements such as an iodonio-Claisen rearrangement, an ipso-rearrangement, and rearrangements performed using iodine(V) are also described.

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“…Domino reactions of epoxy alcohols with hypervalent iodine reagents [14,19] and asymmetric dihydroxylation of enamides have also been investigated [20]. The asymmetric synthesis of (−)-malyngolide was first reported by Mukaiyama [21].…”

Section: Introductionmentioning

confidence: 98%

“…A number of different strategies have been employed in previous syntheses of (+)-tanikolide [3][4][5][6][7][8][9][10] including Sharpless asymmetric epoxidation/dihydroxylation of allylic alcohols [11][12][13][14], the use of enantiopure starting materials D-erythrulose [10], and D-erythrose [9], stereospecific C-H insertion of dichlorocarbene with a chiral secondary alcohol [15], an asymmetric α-alkylation of a β-keto ester and subsequent Bayer-Villiger oxidation [16], α-metallation of ketones and ring closing metathesis [10,12,17,18]. Domino reactions of epoxy alcohols with hypervalent iodine reagents [14,19] and asymmetric dihydroxylation of enamides have also been investigated [20].…”

Section: Introductionmentioning

confidence: 99%

Asymmetric Synthesis of the β-Methyl-Substituted Analogues of (+)-Tanikolide and (–)-Malyngolide

Doran

2015

Asymmetric Synthesis of Bioactive Lactones and the Development of a Catalytic Asymmetric Synthesis of Α-Aryl Ketones

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The asymmetric synthesis of all 4 diastereomers of β-methyl analogues of the marine natural products (+)-tanikolide, which displays antifungal activity, and (−)-malyngolide, which displays antimicrobial activity, has been successfully carried out. The final two diastereomers were synthesised in this Ph.D. project in a 9-step synthesis in 24.9 and 10.8 % overall yields, respectively. Key steps in the synthetic route included Sharpless asymmetric epoxidation and ZrCl 4 -catalysed intramolecular acetalisation as the key steps. The β-methyl substituted analogues were designed to probe the effect the β-methyl group would have on the bioactivity of these compounds. The biological testing of these compounds revealed that none of these analogues showed any antifungal activity however, one of the analogues of malyngolide showed promising activity against MRSA with an MIC of 12.5 μg/mL.

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Domino Reaction of 2,3‐Epoxy‐1‐alcohols and PIFA in the Presence of H₂O and the Concise Synthesis of (+)‐Tanikolide

Abstract: The domino reaction can perform several reactions in a single operation and is a very powerful tool to synthesize organic compounds. The development of new and efficient domino

Cited by 41 publications

References 34 publications

A new era for organic synthesis—highlights of the recent progress

A new era for organic synthesis—highlights of the recent progress

Rearrangements Induced by Hypervalent Iodine

Asymmetric Synthesis of the β-Methyl-Substituted Analogues of (+)-Tanikolide and (–)-Malyngolide

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Domino Reaction of 2,3‐Epoxy‐1‐alcohols and PIFA in the Presence of H2O and the Concise Synthesis of (+)‐Tanikolide

Abstract: The domino reaction can perform several reactions in a single operation and is a very powerful tool to synthesize organic compounds. The development of new and efficient domino

Cited by 41 publications

References 34 publications

A new era for organic synthesis—highlights of the recent progress

A new era for organic synthesis—highlights of the recent progress

Rearrangements Induced by Hypervalent Iodine

Asymmetric Synthesis of the β-Methyl-Substituted Analogues of (+)-Tanikolide and (–)-Malyngolide

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Domino Reaction of 2,3‐Epoxy‐1‐alcohols and PIFA in the Presence of H₂O and the Concise Synthesis of (+)‐Tanikolide