250139-95-8

Upstream product

• 1005-56-7 phenylcarbonochloridothioate 
• 250139-94-7 (1S,3S,8S,9R,13R)-9-hydroxy-2,7,14-trioxatricyclo[11.4.0.0^3,8]heptadec-10-ene 
• 250139-87-8 (2R,3S)-(3-{(2R,3S)-2-[2-(tert-butyldimethylsilyloxy)ethyl]oxan-3-yloxy}oxan-2-yl)methanol 
• 250139-88-9 1-((2R,3S)-3-{(2R,3S)-2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-tetrahydro-pyran-3-yloxy}-tetrahydro-pyran-2-yl)-ethanol 
• 250139-92-5 (1S,3S,8S,13R)-11-acetoxy-2,7,14-trioxatricyclo[11.4.0.0^3,8]heptadecan-9-one 
• 250139-90-3 (2S,3S)-2-(bromoacetyl)-3-[(2R,3S)-2-(2-hydroxyethyl)oxan-3-yloxy]oxane 
• 250139-91-4 {(2R,3S)-3-[(2S,3S)-2-(2-Bromo-acetyl)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-2-yl}-acetaldehyde 
• 250139-93-6 (1S,3S,8S,13R)-2,7,14-trioxatricyclo[11.4.0.0^3,8]heptadec-10-en-9-one 
• 250139-86-7 (2R,3S)-{3-[(2R,3S)-2-vinyloxan-3-yloxy]oxan-2-yl}methanol 

Relevant academic research and scientific papers

A convergent synthesis of the trans-fused hexahydrooxonine ring system and reproduction of conformational behavior shown by ring F of ciguatoxin

A new strategy for the construction of the fused hexahydrooxonine ring system has been developed. The present synthesis involves an intramolecular reaction of γ-alkoxyallylsilane with acetal to form an O-linked oxacycle and a SmI2-mediated intramolecular Reformatsky reaction for constructing an oxonane ring as the key steps. Thermodynamic behavior of the trans-fused hexahydrooxonine ring was clarified for the first time and the conformational alternation was reproduced in the 6-9-6 tricyclic model compound 1 as was observed for that in the ciguatoxin molecule (ring F).