876288-82-3Relevant academic research and scientific papers
Synthesis of the common FGHI-ring part of ciguatoxins
Takizawa, Ayumi,Fujiwara, Kenshu,Doi, Eriko,Murai, Akio,Kawai, Hidetoshi,Suzuki, Takanori
, p. 747 - 751 (2007/10/03)
The common FGHI-ring part (2) of ciguatoxins has been synthesized from the F- and I-ring parts (6 and 5, respectively). The Nozaki-Hiyama-Kishi coupling of 6 with 5 followed by regio- and stereoselective epoxidation at C29 and C30 afforded an epoxide (4),
Convergent synthesis of the common FGHI-ring part of ciguatoxins
Takizawa, Ayumi,Fujiwara, Kenshu,Doi, Eriko,Murai, Akio,Kawai, Hidetoshi,Suzuki, Takanori
, p. 7408 - 7435 (2007/10/03)
Convergent synthesis of the common FGHI-ring part (54) of ciguatoxins was achieved via the following key steps: (i) the Nozaki-Hiyama-Kishi reaction connecting the F-ring part (6) with the I-ring part (7); (ii) regio- and stereoselective epoxidation; (iii) the 6-exo-epoxide opening reaction forming simultaneously the H-ring and the quaternary asymmetric center at C30; (iv) inversion of the C29 stereocenter by a two-step oxidation/reduction process, where the successful inversion depended on proper management of the steric environment of the substrate; and (v) final reductive cyclization constructing the G-ring.
