Synthesis of Paclitaxel. 2. Construction of the ABCD Ring and Formal Synthesis

2015/05/26 by Keisuke Fukaya, Keisuke Kodama, Yuta Tanaka +7 · 4 citations
Medicine · Chemistry · #Cancer Treatment and Pharmacology #Synthetic Organic Chemistry Methods #Microbial Natural Products and Biosynthesis

paper · doi:10.1021/acs.orglett.5b01174

openalex publication_date 2015/05/26 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/09

Abstract

A formal synthesis of the antitumor diterpenoid paclitaxel (Taxol) is described. The ABC ring of paclitaxel, synthesized starting from 1,3-cyclohexanedione and tri-O-acetyl-d-glucal by SmI2-mediated cyclization as the key transformation, was successfully converted to Takahashi's tetracyclic oxetane intermediate. A double Chugaev reaction was employed for introduction of the strained bridgehead olefin, and stereoselective formation of the oxetane ring afforded the known synthetic intermediate, completing the formal synthesis of paclitaxel.

Citations

• Total Synthesis of Baccatin III and Taxol
• Formal Total Synthesis of (−)‐Taxol through Pd‐Catalyzed Eight‐Membered Carbocyclic Ring Formation
• Synthesis of Paclitaxel. 1. Synthesis of the ABC Ring of Paclitaxel by SmI2-Mediated Cyclization
• ThePeterson Olefination Reaction

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• Short, Enantioselective Total Synthesis of Highly Oxidized Taxanes
• Two-Phase Synthesis of Taxol
• A brief overview of classical natural product drug synthesis and bioactivity
• Paclitaxel total synthesis [wikipedia]