DABCO-promoted reaction sequence of β-nitro alcohols and α-oxoaldehydes: construction of diverse tetrahydrofurans and total synthesis of (+)-bruguierol B

IF 4.7 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2025-10-09 DOI:10.1039/d5qo01330e

Yu-Xia Lu, Xue-Jiao Lv, Yankai Liu

引用次数: 0

Abstract

A DABCO-promoted highly efficient reaction sequence has been developed. Under mild conditions, β-nitro alcohols (chiral/achiral or cyclic/acyclic) reacted smoothly with α-oxoaldehydes through a sequential Henry reaction, HNO₂ elimination, and intramolecular hemiketalization to form functionalized hemiketal intermediates. These intermediates serve as oxocarbenium ion precursors, reacting with external or internal nucleophiles diastereoselectively to afford diverse tetrahydrofuran derivatives, including dihydrofuran-3-one, benzoxa[3.2.1]octane, furo[3,2-b]furan, and hexahydrobenzofuranol scaffolds. Notably, this strategy enabled the first total synthesis of (+)-bruguierol B.

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dabco促进β-硝基醇和α-氧醛的反应序列：不同四氢呋喃的构建和(+)-bruguierol B的全合成

建立了dabco催化的高效反应序列。在温和条件下，β-硝基醇（手性/非手性或环性/非环性）与α-氧醛通过连续的亨利反应、HNO 2消除和分子内半池化反应，形成功能化半池化中间体。这些中间体作为氧羰基离子前体，与外部或内部亲核试剂非对映选择性反应生成多种四氢呋喃衍生物，包括二氢呋喃-3- 1、苯并甲[3.2.1]辛烷、呋喃[3,2-b]呋喃和六氢苯并呋喃支架。值得注意的是，该策略使(+)-bruguierol B的首次全合成成为可能。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic Chemistry Frontiers CHEMISTRY, ORGANIC-

CiteScore

7.90

自引率

11.10%

发文量

686

审稿时长

1 months

期刊介绍： Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.