876288-75-4

Upstream product

• 475641-59-9 (Z)-(2R,4aR,6S,7R,11aS)-7-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-phenyl-4a,6,7,8,11,11a-hexahydro-4H-1,3,5-trioxa-benzocyclononene 

Downstream Products

• 876288-76-5 (1R,3S,4R,6Z,9S,11S)-4-benzyloxy-3-benzyloxymethyl-11-phenyl-2,10,12-trioxabicyclo[7.4.0]tridecan-6-ene 
• 876288-79-8 2,2-Dimethyl-propionic acid (Z)-(2R,3S,8R,9S)-8-benzyloxy-9-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2,3,4,7,8,9-hexahydro-oxonin-2-ylmethyl ester 
• 876288-80-1 [(Z)-(2R,3S,8R,9S)-8-Benzyloxy-9-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2,3,4,7,8,9-hexahydro-oxonin-2-yl]-methanol 
• 876288-78-7 2,2-Dimethyl-propionic acid (Z)-(2R,3S,8R,9S)-8-benzyloxy-9-benzyloxymethyl-3-hydroxy-2,3,4,7,8,9-hexahydro-oxonin-2-ylmethyl ester 
• 909001-48-5 C₆₆H₉₁Br₂F₃O₁₁Si₂ 
• 909001-54-3 C₇₃H₉₂Br₂O₁₁Si 
• 909071-90-5 C₆₉H₈₆Br₂O₁₀Si 
• 909001-67-8 C₆₉H₈₄Br₂O₁₀Si 
• 909001-59-8 C₆₉H₈₄Br₂O₁₀Si 
• 909001-51-0 2-[2-[8-benzyloxy-9-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2,3,4,7,8,9-hexahydro-oxonin-2-yl]-1-(4-methoxy-benzyloxy)-ethyl]-7-(4-bromo-benzyloxy)-6-(4-bromo-benzyloxymethyl)-2,9-dimethyl-decahydro-1,5-dioxa-benzocycloocten-3-ol 
• 909001-66-7 C₆₆H₈₆Br₂O₁₁Si 
• 909001-50-9 C₆₆H₈₄Br₂O₁₁Si 
• 909001-65-6 C₆₆H₈₄Br₂O₁₁Si 
• 909001-52-1 2-[2-[8-benzyloxy-9-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2,3,4,7,8,9-hexahydro-oxonin-2-yl]-1-(4-methoxy-benzyloxy)-ethyl]-7-(4-bromo-benzyloxy)-6-(4-bromo-benzyloxymethyl)-2,9-dimethyl-octahydro-1,5-dioxa-benzocycloocten-3-one 

Relevant academic research and scientific papers

Synthesis of the common FGHI-ring part of ciguatoxins

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

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.