Stereoselective Synthesis of Protected 12‐Membered Macrolide Antibiotic 13 <i>E</i> ‐Disciformycin B Aglycone

A stereoselective synthesis of protected macrocyclic lactone core structure of 13 E ‐disciformycin B was accomplished in a convergent fashion employing commercially available (4 S ,5 S )‐2,2‐dimethyl‐1,3‐dioxolane‐4,5‐dicarboxylate, tiglic aldehyde and ( R )‐Roche ester. Key transformations include an Aldol reaction, CBS reduction, Takai olefination, Julia olefination, Nozaki–Hiyama–Kishi (NHK) reaction, and Yamaguchi esterification reaction.

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Publication Details

Journal
European Journal of Organic Chemistry
Published
2025-12-08
DOI
https://doi.org/10.1002/ejoc.202500950
Primary Topic
Synthetic Organic Chemistry Methods
Type
article
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article

Stereoselective Synthesis of Protected 12‐Membered Macrolide Antibiotic 13 E ‐Disciformycin B Aglycone

Naresh Gantasala, Srihari Pabbaraja, Sankara Rao Patta
European Journal of Organic Chemistry
Synthetic Organic Chemistry Methods
article

Stereoselective Synthesis of Protected 12‐Membered Macrolide Antibiotic 13 E ‐Disciformycin B Aglycone

Naresh Gantasala, Srihari Pabbaraja, Sankara Rao Patta
article en

Abstract

A stereoselective synthesis of protected macrocyclic lactone core structure of 13 E ‐disciformycin B was accomplished in a convergent fashion employing commercially available (4 S ,5 S )‐2,2‐dimethyl‐1,3‐dioxolane‐4,5‐dicarboxylate, tiglic aldehyde and ( R )‐Roche ester. Key transformations include an Aldol reaction, CBS reduction, Takai olefination, Julia olefination, Nozaki–Hiyama–Kishi (NHK) reaction, and Yamaguchi esterification reaction.

European Journal of Organic ChemistryVol. 29(3)
University of Minnesota (US), Innovative Design Labs (United States) (US), Indian Institute of Chemical Technology (IN), Academy of Scientific and Innovative Research (IN)
Openalex Percentile: Top 71%
Synthetic Organic Chemistry Methods
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Stereoselective Synthesis of Protected 12‐Membered Macrolide Antibiotic 13 <i>E</i> ‐Disciformycin B Aglycone — Naresh Gantasala, Srihari Pabbaraja, et al. · European Journal of Organic Chemistry (2025) | TGRS Research Map | TGRS