Global InformationKuwajima Taxol total synthesis information
The Kuwajima Taxol total synthesis by the group of Isao Kuwajima of the Tokyo Institute of Technology is one of several efforts in taxol total synthesis published in the 1990s.[1][2] The total synthesis of Taxol is considered a landmark in organic synthesis.
This synthesis is truly synthetic without any help from small biomolecule precursors and also a linear synthesis with molecule ring construction in the order of A, B, C, D. At some point chirality is locked into the molecule via an asymmetric synthesis step which is unique compared to the other efforts. In common with the other efforts the tail addition is based on the Ojima lactam.
The 20 carbon frame is constructed from several pieces: propargyl alcohol (C1, C2, C14), propionaldehyde (C13, C12, C18), isobutyric acid (C15, C16, C17, C11), Trimethyl(phenylthiomethyl)silane (C10), 2-bromobenzaldehyde (C3 to C9), diethylaluminum cyanide (C19) and trimethylsilylmethyl bromide (C20)
- ^ Koichiro Morihira, Ryoma Hara; Soc, Isao Kuwajima; Kawahara, Shigeru; Nishimori, Toshiyuki; Nakamura, Nobuhito; Kusama, Hiroyuki; Kuwajima, Isao (1998). "Enantioselective Total Synthesis of Taxol". J. Am. Chem. Soc. 120 (49): 12980–12981. doi:10.1021/ja9824932.
- ^ Hiroyuki Kusama; Ryoma Hara; Shigeru Kawahara; Toshiyuki Nishimori; Hajime Kashima; Nobuhito Nakamura; Koichiro Morihira; Isao Kuwajima (2000). "Enantioselective Total Synthesis of (−)-Taxol". J. Am. Chem. Soc. 122 (16): 3811–3820. doi:10.1021/ja9939439.