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Pelretin : ウィキペディア英語版
Pelretin

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Pelretin is a synthetic retinoid. It was tested in the 1980s on animals in the hopes that it could be used to eliminate wrinkles.
==Synthesis==

The key reaction in the construction of this compound consists in Wittig reaction of the ylide from phosphonate 3 with the extended aldehyde 4 used in the synthesis of tretinoin itself. Reaction of ''para''-bromomethylbenzoate (1) with triethylphosphite probably proceeds by initial displacement of halogen by phosphorus to give a transient intermediate charged species such as 2. Displacement by one of the ethyl groups on phosphorus by bromide ion from the frist displacement followed by bond reorganization leads to phophonate (3), and EtBr as a by-product. Reaction of the ylide from that product with aldehyde 4 affords the extended polyene. Saponification then yields pelretin.

抄文引用元・出典: フリー百科事典『 ウィキペディア(Wikipedia)
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