Catalytic asymmetric hetero-Diels-Alder route to a key intermediate for the synthesis of calyxin L
Catalytic asymmetric hetero-Diels-Alder route to a key intermediate for the synthesis of calyxin L
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DOI：
10.1016/j.tetasy.2007.10.025
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发表时间：
2007-10-22
影响因子：
--
通讯作者：
Hashimoto, Shunichi
中科院分区：
文献类型：
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作者：
Washio, Takuya;Nambu, Hisanori;Hashimoto, Shunichi
以2，4，6-三取代二氢吡喃为催化剂，通过对映体和非对映体选择性的Hetero-Diels-桤木（HDA）反应、Suzuki-Miyaura偶联反应和立体控制的催化氢化反应为关键步骤，实现了二芳基庚烷类天然产物calyxin L的催化不对称缩甲醛合成。4-（4-苄氧基苯基）-2-三乙基甲硅烷氧基-1，3-丁二烯和（4-苯磺酰氧基苯基）丙炔醛在四[（R）-3-（苯-稠合-邻苯二甲酰亚胺基）-2-哌啶酮]二铑（II），Rh-2（R-BPTPI）（4）催化下的HDA反应，以91%产率和91% ee得到顺式-2，6-二取代四氢吡喃-4-酮。（c）2007 Elsevier Ltd.保留所有权利。
A catalytic asymmetric formal synthesis of diarylheptanoid natural product calyxin L has been achieved by incorporating an enantio- and diastereoselective hetero-Diels-Alder (HDA) reaction, a Suzuki-Miyaura coupling, and a stereocontrolled catalytic hydrogenation of 2,4,6-trisubstituted dihydropyran as the key steps. The HDA reaction between 4-(4-benzyloxyphenyl)-2-triethylsilyloxy-1,3-butadiene and (4-benzenesulfonyloxyphenyl)propynal catalyzed by dirhodium(II) tetrakis[(R)-3-(benzene-fused-phthalimido)-2-piperidinonate], Rh-2(R-BPTPI)(4), provided cis-2,6-disubstituted tetrahydropyran-4-one in 91% yield with 91% ee. (c) 2007 Elsevier Ltd. All rights reserved.