Asymmetric Synthesis of Ampelomin A and &lt;i&gt;ent&lt;/i&gt;-Epiampelomin A

Koyanagi, Yuji; Hamada, Toshiyuki; Iwagawa, Tetsuo; Okamura, Hiroaki

doi:10.5650/jos.ess14212

Cited by 3 publications

(3 citation statements)

References 27 publications

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Section: Total Synthesismentioning

confidence: 68%

“…[115] These metabolites are differentiated by the type of functional group that the oxygenated entities adopt and the stereochemistry of the hydroxyl groups. The absolute configuration of ampelomin A was assigned using the modified Mosher's method and corroborated by an independent synthesis by Okamura et al, [116] while for the other ampelomins, B-G, the absolute configuration of their stereocenters was tentatively assigned based on the spectroscopic data and the biogenetic pathway postulated for the formation of these metabolites. [115] During our studies on the chemoenzymatic synthesis of polyoxygenated compounds starting from cyclohexadienediols produced by biotransformation of toluene, we become interested in the preparation of ampelomins B, D, and E through a chemoenzymatic, stereoselective route.…”

Section: Ampelominsmentioning

confidence: 69%

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Achievements, Challenges, and Scope of Thirty Years of Work on the Biotransformation of Arenes and Their Synthetic Applications

et al. 2022

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Section: Total Synthesismentioning

confidence: 68%

Section: Ampelominsmentioning

confidence: 69%

Achievements, Challenges, and Scope of Thirty Years of Work on the Biotransformation of Arenes and Their Synthetic Applications

et al. 2022

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“…5 These metabolites present a structure of polyoxygenated methyl cyclohexanoids and they are differentiated by the type of functional group that the oxygenated entities adopt and the stereochemistry of the hydroxyl groups. The absolute configuration of ampelomin A was assigned using the modified Mosher's method and corroborated by an independent synthesis by Okamura et al 6 while for the other ampelomins, B−G, the absolute configuration of their stereocenters was tentatively assigned based on the spectroscopic data and the biogenetic pathway postulated for the formation of these metabolites. 5…”

Section: ■ Introductionmentioning

confidence: 66%

Chemoenzymatic Total Synthesis and Structural Revision of Ampelomins B, D, E, and epi-Ampelomin B

et al. 2019

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Enantioselective synthesis of ampelomin B and epi-ampelomin B, D, and E was accomplished starting from toluene, through a chemoenzymatic sequence, in which stereoselective hydrogenation, Mitsunobu reaction, and regio- and stereoselective nucleophilic opening of an epoxide were used as the main transformations. Structural revision and absolute configuration of the natural compounds were carried out.

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Isochroman-3,4-dione and Tandem Aerobic Oxidation of 4-Bromoisochroman-3-one in the Highly Regio- and Diastereoselective Diels–Alder Reaction for the Construction of Bridged Polycyclic Lactones

Mousavi,

Di Mola,

Pierri

et al. 2024

J. Org. Chem.

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Herein we report two processes facilitated by diisopropylethylamine (DIPEA) for the synthesis of novel bridged polycyclic molecule analogues to natural products. The use of 4-bromoisochroman-3-one initiated an autoxidation reaction, followed by a Diels−Alder cycloaddition in the presence of electron-deficient dienophiles. Mechanistic studies revealed isochromane-3,4dione as a key intermediate, which undergoes in situ dienolization/dearomatization followed by a [4 + 2] cycloaddition. Subsequently, the synthesis and direct application of isochromane-3,4-diones in the Diels−Alder reaction enabled the development of an alternative method with an enhanced efficiency and improved atom economy. In addition to chalcones, other enones and common electron-poor alkenes, bearing ester, nitro and cyano electron-withdrawing groups (including both terminal, cis acyclic and cyclic alkenes), were successfully reacted. The mechanism was also investigated, and a subsequent reductive ring opening was successfully carried out.

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Asymmetric Synthesis of Ampelomin A and <i>ent</i>-Epiampelomin A

Cited by 3 publications

References 27 publications

Achievements, Challenges, and Scope of Thirty Years of Work on the Biotransformation of Arenes and Their Synthetic Applications

Achievements, Challenges, and Scope of Thirty Years of Work on the Biotransformation of Arenes and Their Synthetic Applications

Chemoenzymatic Total Synthesis and Structural Revision of Ampelomins B, D, E, and epi-Ampelomin B

Isochroman-3,4-dione and Tandem Aerobic Oxidation of 4-Bromoisochroman-3-one in the Highly Regio- and Diastereoselective Diels–Alder Reaction for the Construction of Bridged Polycyclic Lactones

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