250140-08-0

Upstream product

• 250140-04-6 (2S,3S)-2-acetyl-3-{(2S,3R)-2-[2-(tert-butyldimethylsilyloxy)ethyl]oxan-3-yloxy}oxane 
• 250140-06-8 (1R,3S,8S,11R,13S)-11-acetoxy-2,7,14-trioxatricyclo[11.4.0.0^3,8]heptadecan-9-one 
• 1053652-41-7 (2S,3S)-3-{(2S,3R)-2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-tetrahydro-pyran-3-yloxy}-tetrahydro-pyran-2-carbaldehyde 
• 250140-05-7 (2S,3S)-2-(bromoacetyl)-3-[(2S,3R)-2-(2-hydroxyethyl)oxan-3-yloxy]oxane 
• 250140-03-5 1-((2R,3S)-3-{(2S,3R)-2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-tetrahydro-pyran-3-yloxy}-tetrahydro-pyran-2-yl)-ethanol 
• 250140-02-4 (2R,3S)-(3-{(2S,3R)-2-[2-(tert-butyldimethylsilyloxy)ethyl]oxan-3-yloxy}oxan-2-yl)methanol 
• 161638-76-2 (2R,3S)-{3-[(2S,3R)-2-vinyloxan-3-yloxy]oxan-2-yl}methanol 

Relevant academic research and scientific papers

Construction of fused oxonene ring and reproduction of conformational behavior shown by ring F of ciguatoxin

trans-Fused 6-9-6 tricyclic ether 2 was synthesized and conformational alternation of the oxonene ring was reproduced as was observed for that in the ciguatoxin molecule (ring F). SmI2-promoted intramolecular Reformatsky reaction of O-linked bi

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).