Synthetic Studies on Presporolide, a Putative Enediyne Precursor of Sporolides

Yamashita, Shuji; Terayama, Kanae; Ozeki, Eri; Hayashi, Yujiro; Hirama, Masahiro

doi:10.1021/acs.orglett.7b03670

Cited by 3 publications

(2 citation statements)

References 47 publications

(39 reference statements)

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“…This synthesis aspects are a copper-catalyzed O-arylation reaction of a hindered tertiary alcohol with triarylbismuth reagent, stereoselective production of the strained nine-membered diyne ring; and atroposelective construction of the macrolactone. [209] This synthesis was started from the chiral alcohol 174. [210] The latter after several steps gave compound 175.…”

Section: -Membered Macrolidesmentioning

confidence: 99%

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Applications of Wittig Reaction in the Total Synthesis of Natural Macrolides

et al. 2020

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The Wittig reaction involves the synthesis of an alkene via the conversion of an aldehyde or ketone with the already generated ylide from a phosphonium salt. Significantly, when this important name reaction is employed the desired alkenes are constructed via a predictable manner, thus resultant particularly are useful in the total synthesis of natural products and synthetic complex organic compounds with definite geometric isomers, exhibiting diverse biological potencies. In this review we try to highlight the applications of the Wittig reaction as an efficient and attractive strategy in the total synthesis of macrolides from 2008 to 2020.

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Section: -Membered Macrolidesmentioning

confidence: 99%

“…As a result, this group demonstrated a stereoselective synthesis of the core of presporolide 178 (Scheme 32). [209]…”

Section: -Membered Macrolidesmentioning

confidence: 99%

Applications of Wittig Reaction in the Total Synthesis of Natural Macrolides

et al. 2020

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Direct Access to 9/6‐Fused Cycles via Sequential Hydride Shift Mediated Double C(sp³)−H Bond Functionalization

et al. 2023

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We have developed a sequential hydride shift process involving a [1,8]‐hydride shift. When cinnamylidene malonates having a biphenyl core were treated with 30 mol% Yb(OTf)3 and 10 mol% iPr2NEt, the desired sequential [1,8]‐[1,5]‐hydride shift process proceeded smoothly to afford synthetically challenging nine‐membered carbocycle‐fused piperidine derivatives in good chemical yields (up to 77%). Notably, the desired nine‐membered carbocycles could not be obtained by a single [1,8]‐hydride shift/cyclization process, suggesting that the employment of the sequential system is crucial to achieving the reaction.

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Synthesis of 2,5-Disubstituted Oxazoles from Arylacetylenes and α-Amino Acids through an I2/Cu(NO3)2•3H2O-Assisted Domino Sequence

Wang

Cheng

Xiang

et al. 2019

Synlett

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A new strategy has been developed for the synthesis of 2,5-disubstituted oxazoles from easily available arylacetylenes and α-amino acids in the presence of Cu(NO3)2•3H2O and iodine. This reaction process involves the I2/Cu(NO3)2•3H2O-assisted transformation of arylacetylene to α-iodo acetophenone, Kornblum oxidation to phenylglyoxal, condensation to imine, decarboxylation/annulation/oxidation reaction sequence to approach 2,5-disubstituted oxazoles.

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Synthetic Studies on Presporolide, a Putative Enediyne Precursor of Sporolides

Cited by 3 publications

References 47 publications

Applications of Wittig Reaction in the Total Synthesis of Natural Macrolides

Applications of Wittig Reaction in the Total Synthesis of Natural Macrolides

Direct Access to 9/6‐Fused Cycles via Sequential Hydride Shift Mediated Double C(sp³)−H Bond Functionalization

Synthesis of 2,5-Disubstituted Oxazoles from Arylacetylenes and α-Amino Acids through an I2/Cu(NO3)2•3H2O-Assisted Domino Sequence

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Synthetic Studies on Presporolide, a Putative Enediyne Precursor of Sporolides

Cited by 3 publications

References 47 publications

Applications of Wittig Reaction in the Total Synthesis of Natural Macrolides

Applications of Wittig Reaction in the Total Synthesis of Natural Macrolides

Direct Access to 9/6‐Fused Cycles via Sequential Hydride Shift Mediated Double C(sp3)−H Bond Functionalization

Synthesis of 2,5-Disubstituted Oxazoles from Arylacetylenes and α-Amino Acids through an I2/Cu(NO3)2•3H2O-Assisted Domino Sequence

Contact Info

Product

Resources

About

Direct Access to 9/6‐Fused Cycles via Sequential Hydride Shift Mediated Double C(sp³)−H Bond Functionalization