876288-65-2

Upstream product

• 475641-60-2 (2R,4aR,6S,7R,9S,10aS)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-9-methyl-2-phenyl-octahydro-1,3,5-trioxa-benzocycloocten-7-ol 
• 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 
• 100-39-0 benzyl bromide 
• 876288-86-7 C₇₂H₁₀₀Br₂O₁₁Si₂ 
• 876288-94-7 C₇₆H₉₂Br₂O₁₀Si 
• 876288-93-6 C₆₉H₈₆Br₂O₁₀Si 
• 876288-92-5 C₆₉H₈₄Br₂O₁₀Si 
• 876288-66-3 2-(2-{3-[8-benzyloxy-9-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2,3,4,7,8,9-hexahydro-oxonin-2-ylmethyl]-2-methyl-oxiranyl}-2-triethylsilanyloxy-ethyl)-7-(4-bromo-benzyloxy)-8-(4-bromo-benzyloxymethyl)-5-methyl-oxocan-3-ol 
• 876288-87-8 C₆₄H₉₂Br₂O₁₀Si₂ 
• 876288-85-6 1-{3-[8-benzyloxy-9-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2,3,4,7,8,9-hexahydro-oxonin-2-ylmethyl]-2-methyl-oxiranyl}-2-[7-(4-bromo-benzyloxy)-8-(4-bromo-benzyloxymethyl)-3-(4-methoxy-benzyloxy)-5-methyl-oxocan-2-yl]-ethanol 
• 876288-69-6 (1'R,3'S,4'R,6'R,8'S,10'R)-3'-(tret-butyldimethylsilyloxymethyl)-6'-methyl-10'-phenyl-2',9',11'-trioxabicyclo[6.4.0]dodecan-4'-yl 2,2-dimethylpropionate 
• 876288-81-2 (2R,3S,5Z,8R,9S)-[8-benzyloxy-9-benzyloxymethyl-3-(tret-butyldimethylsilyloxy)-2,3,4,7,8,9-hexahydrooxonin-2-yl]methyl trifluoromethanesulfonate 
• 876288-68-5 (2R,3S,5Z,8R,9S,2'E)-3-benzyloxy-2-benzyloxymethyl-8-(tret-butyldimethylsilyloxy)-9-(3'-iodo-but-2'-ynyl)-2,3,4,7,8,9-hexahydrooxonin 
• 876288-70-9 (2'R,3'S,5'R,7'S,8'R)-2'-(tret-butyldimethylsilyloxymethyl)-7'-hydroxy-8'-hydroxymethyl-5'-methyl-oxocan-3'-yl 2,2-dimethylpropionate 

Relevant academic research and scientific papers

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.

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),