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Literature DB >> 31258206

Synthetic studies towards the penicisulfuranols: Synthesis of an advanced spirocyclic diketopiperazine intermediate.

Kevin M Gayler¹, Kyle M Lambert¹, John L Wood¹.

Abstract

The 2,5-diketopiperazine (DKP) moiety is a core feature of many natural products and medicinally relevant scaffolds. As part of our efforts directed towards a total synthesis of penicisulfuranol B, we have developed and report herein: (1) the preparation of an N-hydroxy diketopiperazine intermediate accessible via a molybdenum-mediated oxidation of a parent diketopiperazine, and (2) further synthetic studies leading to a novel spirocyclic dihydrobenzofuran-containing diketopiperazine.

Entities: CellLine Chemical Disease Gene Species

Keywords: Diketopiperazine; Hydroxamic acid; Oxidation; Penicisulfuranols; Spirocycle

Year: 2019 PMID： 31258206 PMCID： PMC6599588 DOI： 10.1016/j.tet.2019.01.032

Source DB: PubMed Journal: Tetrahedron ISSN： 0040-4020 Impact factor: 2.457

11 in total

1. A Three-Step Entry to the Aspirochlorine Family of Antifungal Agents.

Authors: Zhicai Wu; Lawrence J Williams; Samuel J Danishefsky
Journal: Angew Chem Int Ed Engl Date: 2000-11-03 Impact factor: 15.336

2. Synthesis and activity evaluation of the cyclic dipeptides arylidene N-alkoxydiketopiperazines.

Authors: Xia Tian; Juan Feng; Shi-Ming Fan; Xiao-Li Zhen; Jian-Rong Han; Shou-Xin Liu
Journal: Bioorg Med Chem Date: 2016-08-24 Impact factor: 3.641

3. Synthesis-guided structure revision of the sarcodonin, sarcoviolin, and hydnellin natural product family.

Authors: David W Lin; Takeshi Masuda; Moritz B Biskup; Jonathan D Nelson; Phil S Baran
Journal: J Org Chem Date: 2011-01-20 Impact factor: 4.354

4. Contribution of the intramolecular hydrogen bond to the shift of the pKa value and the oxidation potential of phenols and phenolate anions.

Authors: Daisuke Kanamori; Atsushi Furukawa; Taka-aki Okamura; Hitoshi Yamamoto; Norikazu Ueyama
Journal: Org Biomol Chem Date: 2005-03-10 Impact factor: 3.876

5. Penicisulfuranols A-F, Alkaloids from the Mangrove Endophytic Fungus Penicillium janthinellum HDN13-309.

Authors: Meilin Zhu; Xiaomin Zhang; Huimin Feng; Jiajia Dai; Jing Li; Qian Che; Qianqun Gu; Tianjiao Zhu; Dehai Li
Journal: J Nat Prod Date: 2016-12-19 Impact factor: 4.050

6. The flavan-isoflavan rearrangement: bioinspired synthetic access to isoflavonoids via 1,2-shift-alkylation sequence.

Authors: Kayo Nakamura; Ken Ohmori; Keisuke Suzuki
Journal: Chem Commun (Camb) Date: 2015-03-24 Impact factor: 6.222

7. Structural and biochemical characterization of the cytochrome P450 CypX (CYP134A1) from Bacillus subtilis: a cyclo-L-leucyl-L-leucyl dipeptide oxidase.

Authors: Max J Cryle; Stephen G Bell; Ilme Schlichting
Journal: Biochemistry Date: 2010-08-31 Impact factor: 3.162

Synthetic studies towards the penicisulfuranols: Synthesis of an advanced spirocyclic diketopiperazine intermediate.

1. A Three-Step Entry to the Aspirochlorine Family of Antifungal Agents.

2. Synthesis and activity evaluation of the cyclic dipeptides arylidene N-alkoxydiketopiperazines.

3. Synthesis-guided structure revision of the sarcodonin, sarcoviolin, and hydnellin natural product family.

4. Contribution of the intramolecular hydrogen bond to the shift of the pKa value and the oxidation potential of phenols and phenolate anions.

5. Penicisulfuranols A-F, Alkaloids from the Mangrove Endophytic Fungus Penicillium janthinellum HDN13-309.

6. The flavan-isoflavan rearrangement: bioinspired synthetic access to isoflavonoids via 1,2-shift-alkylation sequence.

7. Structural and biochemical characterization of the cytochrome P450 CypX (CYP134A1) from Bacillus subtilis: a cyclo-L-leucyl-L-leucyl dipeptide oxidase.

8. Hydrogen bonding lowers intrinsic nucleophilicity of solvated nucleophiles.

9. Convergent synthesis and structural confirmation of phellodonin and sarcodonin ε.

10. Novel piperazinediones as antitumor agents.

1. A Ring Expansion Approach To N-oxy-2,5-diketopiperazines.