Synthesis and absolute structure of (-)-umtatin

Yamaguchi S; Kobayashi M; Harada S; Miyazawa M; Hirai Y

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Synthesis and absolute structure of (-)-umtatin

机译：（-）-甜菜碱的合成与绝对结构

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A new preparation of 2-(hydroxymethyl)chromones was developed via the new regio-selective six-membered cyclization of 1-[o-(tert-butyldimethylsiloxy)phenyl]but-2-yn-1-ones by a three-step treatment with 1) diethylamine (activation of the gamma-position), 2) KF-18-crown-6 (deprotection), and 3) silica-gel (cyclization). A naturally occurring chiral hydroxymethylfurochromone, (-)-umtatin, was synthesized starting from chiral (R)-(-)-2-isopropenyl-4,6-dimethooxy-2,3-dihydrobenzofuran. and the absolute structure was determined to R.

机译：通过三步处理1- [邻-（叔丁基二甲基甲硅烷氧基）苯基] but-2-yn-1-one的新的区域选择性六元环化反应，开发了一种2-（羟甲基）色酮的新制备方法用1）二乙胺（激活γ-位置），2）KF-18-crown-6（脱保护）和3）硅胶（环化）。从手性（R）-（-）-2-异丙烯基-4,6-二甲氧基-2,3-二氢苯并呋喃开始合成天然手性羟甲基呋喃二酮（-）-抑菌素。并且绝对结构确定为R。

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来源
《Bulletin of the Chemical Society of Japan》 |2008年第7期|共6页
作者
Yamaguchi S; Kobayashi M; Harada S; Miyazawa M; Hirai Y;
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正文语种 eng
中图分类化学;
关键词
ASYMMETRIC DIHYDROXYLATION; CONFIGURATIONS; REMIROL; KETONES;

机译：不对称二羟基化;构型;视黄醇;酮;

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1. Synthesis and absolute structure of (-)-umtatin [J] . Yamaguchi S, Kobayashi M, Harada S, Bulletin of the Chemical Society of Japan . 2008,第7期

机译：（-）-甜菜碱的合成与绝对结构
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Synthesis and absolute structure of (-)-umtatin

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