Synthesis of Paclitaxel

1. Synthesis of Paclitaxel. 1. Synthesis of the ABC Ring of Paclitaxel by SmI2‑Mediated Cyclization 2. Construction of the ABCD

Краевая Ольга, ВХК РАН, А-31
Synthesis of Paclitaxel.
1. Synthesis of the ABC Ring of Paclitaxel by
SmI2-Mediated Cyclization
2. Construction of the ABCD Ring and Formal
Synthesis
08.12.2015

2. Retrosynthetic analysis of paclitaxel (1)

3. Synthesis of the C Ring of Paclitaxel

4. Preparation of the A−C Rings of Paclitaxel

5. Preparation of the ABC Precursor 4

6. Construction of ABC Ring of Paclitaxel 3

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

8. Synthetic plan for paclitaxel (1) from ABC ring (3)

9. Construction of a Bridgehead Olefin by Chugaev Reaction

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10. Synthesis of Taxoid 4

11. Synthesis of Takahashi’s Oxetane Intermediate

12. 3. Total synthesis of Taxol (baccatinIII) by Takashi

13. Abbreviation

• Thexylborane
• TBDPSCl tBuPh2SiCl
• TPAP Pr4NRuO4
• NMO
• MS4A мол.сита 4A
• 3,5-DMP
• L-selectride
• EDCl
• TBHP

14.

15. Luche reduction mechanism

16. Chugaev reaction mechanism

17. Preparation of 7 from tri-O-acetyl-D-glucal