Proposal for structure revision of pinofuranoxin A through total syntheses of stereoisomers

被引：1

作者：

Ujiie, Kazuki ^{[1
]}

Tanaka, Chiaki ^{[1
]}

Arai, Masayoshi ^{[2
]}

Hashimoto, Masaru ^{[3
]}

Yoshida, Yuki ^{[4
]}

Kawano, Tomikazu ^{[4
]}

Tamura, Satoru ^{[1
]}

机构：

[1] Wakayama Med Univ, Sch Pharmaceut Sci, Lab Nat Prod Chem, 25-1 Shichibancho, Wakayama 6408156, Japan

[2] Osaka Univ, Grad Sch Pharmaceut Sci, Lab Nat Prod Drug Discovery, 1-6 Yamada Oka, Suita, Osaka 5650871, Japan

[3] Hirosaki Univ, Fac Agr & Life Sci, Dept Biochem & Mol Biol, 3 Bunkyo Cho, Hirosaki 0368561, Japan

[4] Iwate Med Univ, Sch Pharm, Dept Med & Organ Chem, 1-1-1 Idai Dori, Yahaba, Iwate 0283694, Japan

来源：

JOURNAL OF NATURAL MEDICINES | 2024年 / 78卷 / 03期

关键词：

Pinofuranoxin A; Asymmetric synthesis; Structure correction; Spectroscopic comparison among stereoisomers; GAMMA-BUTYROLACTONES; STEM BARK; BUTANOLIDES; HYBRID; AKOENSIS; LACTONES; FIELD;

D O I：

10.1007/s11418-024-01810-5

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The relative configuration of the epoxide functionality in pinofuranoxin A (1), alpha-alkylidene-beta-hydroxy-gamma-methyl-gamma-butyrolactone with trans-epoxy side chain isolated by Evidente et al. in 2021, was revised by DFT-based spectral reinvestigations and stereo-controlled synthesis. The present investigation demonstrates the difficulty of the configurational elucidation of the stereogenic centers on the conformationally flexible acyclic side-chains. Sharpless's enantioselective epoxidations and dihydroxylations were quite effective in the reinvestigations of the configurations. As our syntheses made all diastereomers available, these would be quite effective in the next structure-biological activity relationship studies.

引用

页码：608 / 617

页数：10

共 40 条

[1] Chloro polyketides from the cultured fungus (Aspergillus) separated from a marine sponge [J].