253172-09-7

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 
• 253172-13-3 (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-((Z)-but-2-enyl)-5-methyl-oxocan-3-yl ester 
• 253172-17-7 C₂₃H₄₆O₅Si₂ 
• 474125-24-1 (5R,7S,8R,9S,10S)-7-Benzyloxymethyl-8-methoxymethoxy-9,10-dimethyl-1,6-dioxa-spiro[4.5]decane 
• 474125-23-0 (3S,4S,5R,6S)-6-Benzyloxymethyl-5-methoxymethoxy-3,4-dimethyl-tetrahydro-pyran-2-one 
• 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 
• 253172-11-1 7-benzyloxy-2-[2-benzyloxy-2-(8-methoxymethoxy-9,10-dimethyl-1,6-dioxa-spiro[4.5]dec-7-yl)-1-methyl-ethyl]-6-benzyloxymethyl-9-methyl-4,4a,6,7,8,9,10,10a-octahydro-1,5-dioxa-benzocyclooctene 
• 261776-53-8 (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 
• 474125-25-2 (5R,7S,8R,9S,10S)-7-((1S,2R)-1-Benzyloxy-2-methyl-but-3-enyl)-8-methoxymethoxy-9,10-dimethyl-1,6-dioxa-spiro[4.5]decane 
• 253172-19-9 (1S,2R)-1-((5R,7S,8R,9S,10S)-8-Methoxymethoxy-9,10-dimethyl-1,6-dioxa-spiro[4.5]dec-7-yl)-2-methyl-but-3-en-1-ol 
• 253172-18-8 ((5R,7S,8R,9S,10S)-8-Methoxymethoxy-9,10-dimethyl-1,6-dioxa-spiro[4.5]dec-7-yl)-methanol 

Downstream Products

• 474125-40-1 C₄₁H₅₈O₁₀ 
• 474125-41-2 C₄₂H₅₇NO₉ 
• 474125-38-7 C₃₃H₄₈O₉ 
• 474125-39-8 C₄₁H₅₆O₁₀ 
• 474125-43-4 C₄₅H₆₄O₁₀ 
• 474125-45-6 C₄₆H₆₄O₁₀ 
• 474125-44-5 C₄₅H₆₄O₁₁ 
• 474125-42-3 C₄₇H₆₆O₁₁ 

Relevant academic research and scientific papers

An improved synthesis of the C42–C52 segment of ciguatoxin 3C

In our previously reported method for the construction of the IJKLM-ring of ciguatoxin 3C (CTX3C), the lengthy synthetic process for the intermediate C42–C52 (L-ring) segment was problematic. Therefore, a new and improved procedure for the C42–C52 segment, having modified protecting groups, was developed. The new route includes a chirality transferring Ireland-Claisen rearrangement for the construction of the vicinal dimethyl branching at C47–48, a one-pot cyclization process for the establishment of the stereocenters at C45 and C46 as well as the γ-hydroxy δ-lactone framework corresponding to the L-ring, and Brown's asymmetric crotylboration for the installation of the stereocenters at C43 and C44. The new C42–C52 segment was successfully coupled with the previously reported C32–C41 (I-ring) segment to produce the IJKLM-ring.

Convergent synthesis of the IJKLM-ring part of ciguatoxin CTX3C

Convergent synthesis of the IJKLM-ring part (2) of ciguatoxin CTX3C has been achieved from the I-ring and the L-ring parts (4 and 5) in total eight steps in 27% overall yield. The carbanion derived from 4, stabilized by a dimethyldithioacetal S-oxide grou

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.

Convergent synthesis of the IJKLM ring fragment of ciguatoxin CTX3C

The IJKLM ring fragment of CTX3C, an important member of the ciguatoxin family, was synthesized via ring-closing metathesis using the Tebbe reagent and an improved method of reductive hydroxy ketone cyclization.