Diastereoselective synthesis of ω-phosphonic acid analogues of 4-arylkainoids

Yuasa, Yoko; Fujimaki, Nobuko; Yokomatsu, Tsutomu; Ando, Jun; Shibuya, Shiroshi

doi:10.1039/a804666b

Cited by 10 publications

(3 citation statements)

References 10 publications

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“…Successful examples of cyclization involving 1-amidoalkyl radicals generated from N,S-acetals onto vinylphosphonates have been reported by Shibuya. 213 Hart and co-workers reported a spectacular example of cyclization onto an electron deficient alkene in their synthesis of gelsemine. On a model substrate, cyclization onto a non-activated alkene afforded exclusively the product of reductive desulfurization (Scheme 94, eqn (a)).…”

Section: Cyclization Reactionsmentioning

confidence: 99%

Thiols, thioethers, and related compounds as sources of C-centred radicals

2013

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Due to their stability, availability and reactivity, sulfides are particularly attractive sources of carbon-centered radicals. However, their reactivity in homolytic substitution processes is strongly reduced when compared with the corresponding selenides or halides. Despite this, sulfur-containing compounds can be engineered so that they become effective agents in radical chain reactions. A detailed description of the reactivity of organo-sulfur compounds is reported here with the aim of providing clear guidance on the scope and limitation of their use as radical precursors in chain reactions.

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Section: Cyclization Reactionsmentioning

confidence: 99%

Thiols, thioethers, and related compounds as sources of C-centred radicals

2013

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“…The route to 9 , the core of cladobotryal, is based on the two subunits γ-butyrolactone ( 12 ) and the known β-amino aldehyde 13 , which we made (Scheme ) by the sequence 19 → 18 → 13 , along lines reported 8 in the literature, but with minor modifications. We found it convenient to prepare the intermediate 19 by a route different from those previously reported. , The readily available alcohol 14 was converted (91%) into the phthalimide 15 under Mitsunobu conditions. Treatment with N 2 H 4 ·H 2 O in EtOH liberated amine 16 (97%), which was protected (100%) as its N -Boc derivative (Boc 2 O, aqueous acetone, NaHCO 3 , 16 → 17 ).…”

Section: Introductionmentioning

confidence: 99%

Model Studies and First Synthesis of the Antifungal and Antibacterial Agent Cladobotryal

Clive

Huang

2004

J. Org. Chem.

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The antifungal and antibacterial agent cladobotryal (1) was synthesized by a convergent route from lactone 31 and aldehyde 13, a key step in the elaboration of the pyridinone ring being conversion of a Boc group on nitrogen into a CO(2)SiPr-i(3) group. The simple model compounds 9 and 10, representing the core of cladobotryal and of 5, respectively, were prepared as support studies for making the natural product.

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“…Thus, the (α,α-difluoroalkyl)phosphonate analogue of L-phosphoserine was obtained by basemediated oxazolidinone ring cleavage of 98, followed by the oxidation under the Corey-Schmidt conditions that yield the desired protected phosphoserine analog 99 [53] (Scheme 26). In the synthesis of phosphonic acid analogue of kainoids, the same strategy is used to build a synthetic scheme, which was implemented at the final stage of multistage transformation [54]. Cleavage of the oxazolidinone ring of compound 100 was achieved with aqueous base with subsequent protection of the nitrogen atom with a tertbutoxycarbonyl group to yield compound 101 (Scheme 27).…”

Section: Synthesis Based On Oxazolidine Derivativesmentioning

confidence: 99%

1,3-Oxazoles as precursors of phosphorylated amino acids and peptidomimetics

et al. 2022

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The design and development of new phosphorus-containing amino acids and peptidomimetics have been attracting considerable attention due to their value as intermediates in the synthesis of biologically active compounds and the prospects for further pharmacological applications. 1,3-Oxazole derivatives, as masked peptides, constitute an important group of amino acid precursors that are widely used in contemporary organic synthesis. This review presents the 1,3-oxazole-based synthetic strategies of phosphorylated amino acids and peptides that have been published in both journal and patent literature. We have focused specifically on the synthesis of 4-phosphorylated 1,3-oxazoles as precursors of phosphopeptide mimetics containing the peptide chain with a non-terminal phosphono group due to the growing interest in finding efficient methods for the synthesis of this little-studied class of compounds

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Diastereoselective synthesis of ω-phosphonic acid analogues of 4-arylkainoids

Cited by 10 publications

References 10 publications

Thiols, thioethers, and related compounds as sources of C-centred radicals

Thiols, thioethers, and related compounds as sources of C-centred radicals

Model Studies and First Synthesis of the Antifungal and Antibacterial Agent Cladobotryal

1,3-Oxazoles as precursors of phosphorylated amino acids and peptidomimetics

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