page_title: Holton Taxol total synthesis
hierarchical_section_title: Holton Taxol total synthesis
caption_attribution_description: English: Holton Taxol total synthesis overview from raw material perspective
context_page_description: The Holton Taxol total synthesis, published by Robert A. Holton and his group at Florida State University in 1994 was the first total synthesis of Taxol.
  The Holton Taxol total synthesis is a good example of a linear synthesis starting from commercially available natural compound patchoulene oxide.
  This epoxide can be obtained in two steps from the terpene patchoulol and also from borneol. The reaction sequence is also enantioselective, synthesizing-Taxol from-patchoulene oxide or-Taxol from-borneol with a reported specific rotation of +- 47°. The Holton sequence to Taxol is relatively short compared to that of the other groups. One of the reasons is that patchoulene oxide already contains 15 of the 20 carbon atoms required for the Taxol ABCD ring framework.
  Other raw materials required for this synthesis include 4-pentenal, m-chloroperoxybenzoic acid, methyl magnesium bromide and phosgene. Two key chemical transformations in this sequence are a Chan rearrangement and a sulfonyloxaziridine enolate oxidation.
context_section_description: The Holton Taxol total synthesis, published by Robert A. Holton and his group at Florida State University in 1994 was the first total synthesis of Taxol (generic name: paclitaxel).
  The Holton Taxol total synthesis is a good example of a linear synthesis starting from commercially available natural compound patchoulene oxide.
  This epoxide can be obtained in two steps from the terpene patchoulol and also from borneol. The reaction sequence is also enantioselective, synthesizing (+)-Taxol from (−)-patchoulene oxide or (−)-Taxol from (−)-borneol with a reported specific rotation of +- 47° (c=0.19 / MeOH). The Holton sequence to Taxol is relatively short compared to that of the other groups (46 linear steps from patchoulene oxide). One of the reasons is that patchoulene oxide already contains 15 of the 20 carbon atoms required for the Taxol ABCD ring framework.  
  Other raw materials required for this synthesis include 4-pentenal, m-chloroperoxybenzoic acid, methyl magnesium bromide and phosgene. Two key chemical transformations in this sequence are a Chan rearrangement and a sulfonyloxaziridine enolate oxidation.
caption: Holton Taxol total synthesis overview from raw material perspective
exif: {}