Forging the tricyclic core framework of euphordraculoate B <i>via</i> a Barbier-type allyl addition

A novel strategy for the synthesis of an advanced intermediate <i>en route</i> to the tigliane derivative euphordraculoate B was described, which led to the successful construction of the 5/5/6 tricyclic core framework as well as the multiple consecutive stereocenters on the skeleton. Key steps of the strategy include a chlorination reaction, an aldol reaction, and a Barbier-type allyl addition.

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Publication Details

Journal
Organic & Biomolecular Chemistry
Published
2024-11-27
DOI
https://doi.org/10.1039/d4ob01743a
Primary Topic
Chemical synthesis and alkaloids
Type
article
Field-Weighted Citation Impact
0.00
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article

Forging the tricyclic core framework of euphordraculoate B via a Barbier-type allyl addition

Pingping Tang, Zhaobin Sun, Longhui Meng, Jingjing Liu et al.
Organic & Biomolecular Chemistry
Chemical synthesis and alkaloids
article

Forging the tricyclic core framework of euphordraculoate B via a Barbier-type allyl addition

Pingping Tang, Zhaobin Sun, Longhui Meng, Jingjing Liu, Yumin Hou, Qianwen Huang
article en

Abstract

A novel strategy for the synthesis of an advanced intermediate <i>en route</i> to the tigliane derivative euphordraculoate B was described, which led to the successful construction of the 5/5/6 tricyclic core framework as well as the multiple consecutive stereocenters on the skeleton. Key steps of the strategy include a chlorination reaction, an aldol reaction, and a Barbier-type allyl addition.

Organic & Biomolecular ChemistryVol. 23(3)
Nankai University (CN)
Openalex Percentile: Top 84%
Chemical synthesis and alkaloids
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