Bi(III)-Catalyzed Synthesis of Substituted Furans from Hydroxy-oxetanyl Ketones: Application to Unified Total Synthesis of Shikonofurans J, D, E, and C

被引：5

作者：

Kataria, Priyanka ^{[1
,2
]}

Sahoo, Shubhranshu Shekhar ^{[3
]}

Kontham, Ravindar ^{[1
,2
]}

机构：

[1] CSIR, Organ Chem Div, Natl Chem Lab, Pune 411008, India

[2] Acad Sci & Ind Res AcSIR, Ghaziabad 201002, India

[3] CSIR, Biochem Sci Div, Natl Chem Lab, Pune 411008, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 11期

关键词：

LITHOSPERMUM-ERYTHRORHIZON; ALLYL ETHERS; SHIKONIN; DEPROTECTION; DERIVATIVES; MILD; STRATEGY; ALKANNIN;

D O I：

10.1021/acs.joc.3c00549

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report an improved synthetic protocol for hydroxymethyl-derivedpolysubstituted furans employing Bi-(III)-catalyzed dehydrative cycloisomerizationof alpha-hydroxy oxetanyl ketones. This procedure provides rapidaccess (within 5 min) to highly substituted furans with exceptionalfunctional group diversity, excellent yields, generality, scalability,and operationally simple reaction conditions. Further, it demonstratedthe utility of this method in the first enantioselective total synthesisof furyl-hydroquinone-derived biologically potent natural productsshikonofurans J, D, E, and C in seven linear steps, starting fromreadily available building blocks of 2,5-dihydroxy acetophenone and3-oxetanone employing chiral-phosphoric acid (TRIP)-catalyzed asymmetricprenylation as a key step to induce the chirality.

引用

页码：7328 / 7346

页数：19