474125-24-1

Upstream product

• 474125-23-0 (3S,4S,5R,6S)-6-Benzyloxymethyl-5-methoxymethoxy-3,4-dimethyl-tetrahydro-pyran-2-one 
• 196392-89-9 (3S,4S,5S)-5-((R)-2-Benzyloxy-1-iodo-ethyl)-3,4-dimethyl-dihydro-furan-2-one 
• 196393-04-1 (3S,4S,5R,6S)-6-Benzyloxymethyl-5-hydroxy-3,4-dimethyl-tetrahydro-pyran-2-one 

Downstream Products

• 474125-42-3 C₄₇H₆₆O₁₁ 
• 474125-44-5 C₄₅H₆₄O₁₁ 
• 474125-45-6 C₄₆H₆₄O₁₀ 
• 474125-43-4 C₄₅H₆₄O₁₀ 
• 474125-36-5 C₄₇H₆₂O₉ 
• 474125-39-8 C₄₁H₅₆O₁₀ 
• 474125-38-7 C₃₃H₄₈O₉ 
• 337309-16-7 (2S,3S)-3-Benzyloxy-3-((5R,7S,8R,9S,10S)-8-methoxymethoxy-9,10-dimethyl-1,6-dioxa-spiro[4.5]dec-7-yl)-2-methyl-propionic acid (2R,3S,5S,7R,8S)-7-benzyloxy-8-benzyloxymethyl-2-(2,2-bis-phenylsulfanyl-ethyl)-5-methyl-oxocan-3-yl ester 
• 474125-41-2 C₄₂H₅₇NO₉ 
• 474125-40-1 C₄₁H₅₈O₁₀ 
• 261776-54-9 (2R,4aR,6S,7R,9S,10aS)-7-Benzyloxy-2-[(1S,2S)-2-benzyloxy-2-((5R,7S,8R,9S,10S)-8-methoxymethoxy-9,10-dimethyl-1,6-dioxa-spiro[4.5]dec-7-yl)-1-methyl-ethyl]-6-benzyloxymethyl-9-methyl-octahydro-1,5-dioxa-benzocycloocten-3-one 
• 253172-22-4 (2S,4aR,6S,7R,9S,10aS)-7-Benzyloxy-2-[(1S,2S)-2-benzyloxy-2-((5R,7S,8R,9S,10S)-8-methoxymethoxy-9,10-dimethyl-1,6-dioxa-spiro[4.5]dec-7-yl)-1-methyl-ethyl]-6-benzyloxymethyl-9-methyl-octahydro-1,5-dioxa-benzocycloocten-3-one 
• 474125-48-9 (4aR,6S,7R,9S,10aS)-7-Benzyloxy-2-[(1S,2S)-2-benzyloxy-2-((5R,7S,8R,9S,10S)-8-methoxymethoxy-9,10-dimethyl-1,6-dioxa-spiro[4.5]dec-7-yl)-1-methyl-ethyl]-6-benzyloxymethyl-9-methyl-decahydro-1,5-dioxa-benzocycloocten-3-ol 
• 253172-24-6 (2R,4aR,6S,7R,9S,10aS)-7-Benzyloxy-2-[(1S,2S)-2-benzyloxy-2-((5R,7R,8R,9S,10S)-8-hydroxy-9,10-dimethyl-1,6-dioxa-spiro[4.5]dec-7-yl)-1-methyl-ethyl]-6-benzyloxymethyl-9-methyl-octahydro-1,5-dioxa-benzocycloocten-3-one 

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.

Convergent synthesis of the HIJKLM ring fragment of ciguatoxin CTX3C

Ciguatoxin CTX3C is a representative congener of the ciguatoxins, which are known to be the principal causative agents of ciguatera food poisoning. The structure of CTX3C spans more than 3nm and is characterized by 13 ether rings. To attain a practical construction of this molecule, efficient supplies of the structural fragments are crucial. Herein we report the convergent synthesis of the HIJKLM ring fragment and present a new carbonyl olefination protocol to cyclize the J ring using low-valent titanium.