Synthesis of Paclitaxel. 1. Synthesis of the ABC Ring of Paclitaxel by SmI2-Mediated Cyclization

2015/05/26 by Keisuke Fukaya, Yuta Tanaka, Ayako Sato +13 · 5 citations
Medicine · Chemistry · #Cancer Treatment and Pharmacology #Synthetic Organic Chemistry Methods #Microbial Natural Products and Biosynthesis

paper · doi:10.1021/acs.orglett.5b01173

openalex publication_date 2015/05/26 · openalex created_date 2016/06/24 · openalex updated_date 2026/07/09

Abstract

A convergent synthesis of the ABC ring of antitumor natural product paclitaxel (Taxol) is described. SmI2-mediated reductive cyclization of an allylic benzoate possessing an aldehyde function, synthesized from tri-O-acetyl-d-glucal and 1,3-cyclohexanedione, smoothly afforded the highly strained 6-8-6 tricarbocyclic structure in 66% yield.

Citations

• First total synthesis of taxol. 2. Completion of the C and D rings
• Total Synthesis of Baccatin III and Taxol
• The Pinene Path to Taxanes. 5. Stereocontrolled Synthesis of a Versatile Taxane Precursor
• First total synthesis of taxol. 1. Functionalization of the B ring
• Formal Total Synthesis of (−)‐Taxol through Pd‐Catalyzed Eight‐Membered Carbocyclic Ring Formation
• A New Method for the Synthesis of Baccatin III

Cited by

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