499237-58-0

Upstream product

• 337309-33-8 ((2R,3S,5S,7R,8S)-7-Benzyloxy-8-benzyloxymethyl-5-methyl-3-triethylsilanyloxy-oxocan-2-yl)-acetonitrile 
• 337309-17-8 [(2R,4S,5R)-4-Allyl-2-(4-methoxy-phenyl)-[1,3]dioxan-5-yloxy]-acetic acid tert-butyl ester 
• 337309-32-7 (2R,4aR,6S,9R,10aS)-6-Hydroxymethyl-2-(4-methoxy-phenyl)-9-methyl-hexahydro-1,3,5-trioxa-benzocycloocten-7-one 
• 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 
• 337309-18-9 (R)-2-[(2R,4S,5R)-4-Allyl-2-(4-methoxy-phenyl)-[1,3]dioxan-5-yloxy]-3-hydroxy-pent-4-enoic acid tert-butyl ester 
• 337309-22-5 (2R,4aR,6S,9R,10aS)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2-(4-methoxy-phenyl)-9-methyl-hexahydro-1,3,5-trioxa-benzocycloocten-7-one 
• 474125-29-6 (2R,4aR,6S,7R,9S,10aS)-7-Benzyloxy-6-benzyloxymethyl-2-(4-methoxy-phenyl)-9-methyl-octahydro-1,3,5-trioxa-benzocyclooctene 
• 474125-31-0 (2S,3S,5R,7R,8S)-7-Benzyloxy-8-benzyloxymethyl-2-iodomethyl-5-methyl-oxocan-3-ol 
• 337309-24-7 ((2R,3S,5R,7R,8S)-7-Benzyloxy-8-benzyloxymethyl-3-hydroxy-5-methyl-oxocan-2-yl)-acetonitrile 
• 474125-30-9 (2R,3S,5R,7R,8S)-7-Benzyloxy-8-benzyloxymethyl-2-hydroxymethyl-5-methyl-oxocan-3-ol 

Downstream Products

• 474125-35-4 [(2R,3S,5S,7R,8S)-7-Benzyloxy-8-benzyloxymethyl-2-(2,2-bis-phenylsulfanyl-ethyl)-5-methyl-oxocan-3-yloxy]-triethyl-silane 
• 337309-25-8 (2R,3S,5R,7R,8S)-7-Benzyloxy-8-benzyloxymethyl-2-(2,2-bis-phenylsulfanyl-ethyl)-5-methyl-oxocan-3-ol 
• 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 

Relevant academic research and scientific papers

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.

Practical entry into the HIJKLM ring segment of ciguatoxin CTX3C

The HIJKLM ring segment (27) of the right half portion of ciguatoxin CTX3C (1) has been synthesized using a ring-closing reaction mediated by a low-valent titanium reagent.