596792-40-4

Upstream product

• 474125-28-5 (2R,4aR,6S,7R,9S,10aS)-6-Hydroxymethyl-2-(4-methoxy-phenyl)-9-methyl-octahydro-1,3,5-trioxa-benzocycloocten-7-ol 
• 685118-07-4 [(2S,3R,4aS,6R,7S,9S,10aR)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-2,9-dimethyl-7-triethylsilanyloxy-3-triisopropylsilanyloxy-decahydro-1,5-dioxa-benzocycloocten-6-yl]-acetaldehyde 
• 596792-68-6 (2S,3R,4aS,6S,7S,9R,10aR)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-iodomethyl-2,9-dimethyl-3-triisopropylsilanyloxy-decahydro-1,5-dioxa-benzocycloocten-7-ol 
• 596792-54-0 [(2S,3R,4aS,6R,7S,9S,10aR)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-2,9-dimethyl-7-triethylsilanyloxy-3-triisopropylsilanyloxy-decahydro-1,5-dioxa-benzocycloocten-6-yl]-acetonitrile 
• 596792-52-8 (3R,4aS,6S,7aR,9S,10R,11aS,12aR)-9-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(4-methoxy-phenyl)-6,9-dimethyl-10-triisopropylsilanyloxy-decahydro-2,4,8,12-tetraoxa-dibenzo[a,d]cyclooctene 
• 596792-69-7 [(2S,3R,4aS,6R,7S,9R,10aR)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-7-hydroxy-2,9-dimethyl-3-triisopropylsilanyloxy-decahydro-1,5-dioxa-benzocycloocten-6-yl]-acetonitrile 
• 596792-53-9 (2S,3R,4aS,6R,7S,9R,10aR)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-hydroxymethyl-2,9-dimethyl-3-triisopropylsilanyloxy-decahydro-1,5-dioxa-benzocycloocten-7-ol 
• 596792-67-5 (3R,4aS,6S,7aR,9S,10R,11aS,12aR)-9-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(4-methoxy-phenyl)-6,9-dimethyl-decahydro-2,4,8,12-tetraoxa-dibenzo[a,d]cycloocten-10-ol 
• 596792-51-7 (3R,4aS,6S,7aR,9S,11aS,12aR)-9-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(4-methoxy-phenyl)-6,9-dimethyl-octahydro-2,4,8,12-tetraoxa-dibenzo[a,d]cycloocten-10-one 
• 596792-55-1 (2S,3R,4aS,6R,7S,9S,10aR)-6-(2,2-Bis-phenylsulfanyl-ethyl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-2,9-dimethyl-7-triethylsilanyloxy-3-triisopropylsilanyloxy-decahydro-1,5-dioxa-benzocyclooctene 
• 596792-50-6 (2R,4aR,6S,7R,9R,10aS)-6-[(2S,3R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-3-methyl-2-(toluene-4-sulfonyl)-oxiranylmethyl]-2-(4-methoxy-phenyl)-9-methyl-7-triethylsilanyloxy-octahydro-1,3,5-trioxa-benzocyclooctene 

Downstream Products

• 685117-95-7 C₇₉H₁₀₈O₁₁S₂Si₂ 
• 685118-02-9 C₆₅H₉₄O₉Si₂ 
• 685118-01-8 C₆₆H₉₆O₁₀Si₂ 
• 685117-96-8 C₆₇H₉₈O₁₀Si₂ 
• 685118-08-5 C₆₇H₉₈O₁₁Si₂ 
• 685117-98-0 C₆₇H₉₈O₁₁Si₂ 
• 685118-00-7 C₆₇H₁₀₀O₁₁Si₂ 
• 685117-99-1 C₆₇H₉₈O₁₁Si₂ 

Relevant academic research and scientific papers

A New Stereoselective Synthesis of Ciguatoxin Right Wing Fragments

The right wings (13 and 14) of ciguatoxins were synthesized highly stereoselectively. Key transformations in the synthesis are (i) an oxiranyl anion strategy to attach the H ring, (ii) intramolecular carbonyl olefination to cyclize the J ring, (iii) regio- and stereoselective reduction of the epoxyacetal to install the C42-stereocenter, and (iv) stereoselective reductive etherification to construct the K ring. The present procedure greatly improved the stereoselectivity and efficiency in comparison to a previous synthesis. Remarkably, only 23 steps were required from monocyclic I ring 5 to construct the ciguatoxin right wings. The high practicality of the present synthesis ensures a sufficient supply of these complex fragments for total syntheses and biomedical applications.

A concise route to the right wing of ciguatoxin

A concise route to the HIJKLM-ring fragment 10 of ciguatoxin (CTX) and 51-hydroxyCTX3C was developed in which oxiranyl anion addition and intramolecular carbonyl olefination were utilized as key transformations. The present procedure requires only 23 steps from the I-ring 5, while 35 steps were employed in a previous synthesis of the corresponding right wing 11 of CTX3C. The high efficiency of the present synthesis ensures a supply of 10 for total synthesis and biomedical applications.