Stereoselective Approach toward Ophiodilactones Based on an Intramolecular [2 + 2] Cycloaddition Reaction

Hatakeyama, Susumi; Matsubara, Takaaki; Ishihara, Jun

doi:10.3987/com-14-s(k)32

HETEROCYCLES

2015

DOI: 10.3987/com-14-s(k)32

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Stereoselective Approach toward Ophiodilactones Based on an Intramolecular [2 + 2] Cycloaddition Reaction

Susumi Hatakeyama¹,

Takaaki Matsubara²,

Jun Ishihara³

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Cited by 3 publications

(1 citation statement)

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“…The cycloaddition of ketenes to alkenes is a generally popular method for the synthesis of cyclobutanone derivatives . Although the intramolecular [2 + 2] cycloadditions of ketenes to alkenes generate synthetically useful polycyclic compounds with a high degree of regio- and stereocontrol, this method has been applied by a few groups for the synthesis of natural products . Heterosubstituted ketenes, such as the alkyl(phenylthio)ketenes, have shown enhanced reactivity toward functional groups (Scheme A) .…”

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confidence: 99%

Intramolecular [2 + 2] Cycloadditions of Alkyl(phenylthio)ketenes: Total Synthesis of (+)-Sphaerodiol

Wang

Huang

et al. 2018

Org. Lett.

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Intramolecular [2 + 2] Cycloadditions of Alkyl(phenylthio)ketenes: Total Synthesis of (+)-Sphaerodiol

Wang

Huang

et al. 2018

Org. Lett.

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Substituted ketenes offer exceptional carbon bases in gas phase: Computational study by density functional theory method

Golpayegani

Mirjafary

Saeidian

et al. 2020

J of Physical Organic Chem

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In the present study, ketene derivatives with cyclopropene and methylenecyclopropene substituents have been investigated by B3LYP/6‐311+G(d,p) level of theory to evaluate their suitability as powerful carbon superbases. The protonation at C (sp) site provides new neutral organic bases with proton affinities (PAs) = 879–1,218 kJ/mol, in which some are more basic than 1,8‐bis(dimethylamino)‐naphthalene, whose gas‐phase PA of 1,028 kJ/mol is considered the threshold of superbasicity. The PAs of designed ketenes were amplified by substitution of electron‐releasing groups such as methyl and dimethylamino on the molecular framework. Two indices of aromaticity, nucleus‐independent chemical shift and harmonic oscillator model of aromaticity, were also used for elucidation of ketene basicity, which reveals that a cyclopropene ring on the proposed ketene derivatives becomes aromatic upon protonation.

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Stereocontrolled Total Synthesis of Biologically Active Natural Products

Hatakeyama

2018

YAKUGAKU ZASSHI

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This review article describes the total syntheses of englerin A, ophiodilactones A and B, marinomycin A, N-methylwelwitindolinone C isothiocyanate, tirandamycins A D, and tirandalydigin, which possess intriguing biological activities and challenging structures with characteristic ring systems. The focus is on the synthetic methodologies that lead to the highly stereocontrolled assembly of these natural products.Key words-total synthesis; natural product; stereocontrolled synthesis

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Stereoselective Approach toward Ophiodilactones Based on an Intramolecular [2 + 2] Cycloaddition Reaction

Cited by 3 publications

References 16 publications

Intramolecular [2 + 2] Cycloadditions of Alkyl(phenylthio)ketenes: Total Synthesis of (+)-Sphaerodiol

Intramolecular [2 + 2] Cycloadditions of Alkyl(phenylthio)ketenes: Total Synthesis of (+)-Sphaerodiol

Substituted ketenes offer exceptional carbon bases in gas phase: Computational study by density functional theory method

Stereocontrolled Total Synthesis of Biologically Active Natural Products

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