Synthesis of the ABC-ring models of goniodomin A: preference for the unnatural configuration at C11 of the BC-ring in a non-macrocyclic model system
Synthesis of the ABC-ring models of goniodomin A: preference for the unnatural configuration at C11 of the BC-ring in a non-macrocyclic model system
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DOI：
10.1016/j.tetlet.2008.03.082
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发表时间：
2008-05-12
影响因子：
1.8
通讯作者：
Suzuki, Takanori
中科院分区：
文献类型：
--
作者：
Katagiri, Takahiro;Fujiwara, Kenshu;Suzuki, Takanori
为了证实goniodomin A（1）的ABC环的天然相对立体化学，相应的三种立体异构体化合物，（2R，5S，6S，7S，9S，11R，15S）-，（2R，5S，6S，7R，9R，11S，15R）-，和（2 R，5S，6S，7 R，9 R，11 R，15 S）-异构体（分别为2、3和5）使用Nozaki-Hiyama-Kishi反应作为关键步骤立体选择性地合成。在酸催化的螺缩醛化反应条件下，由一种常见的酮二醇底物生成5的过程中，没有检测到一种（2 R，5S，6S，7 R，9 R，11 S，15 S）-异构体（4），该异构体对应于Sasaki最近提出的I的绝对构型。这可能是由于缺乏大循环框架。(c)2008爱思唯尔有限公司保留所有权利。
To confirm the natural relative stereochemistry of the ABC-ring of goniodomin A (1), the corresponding three stereoisomeric compounds, (2R,5S,6S,7S,9S,11R,15S)-, (2R,5S,6S,7R,9R,11S,15R)-, and (2R,5S,6S,7R,9R,11R,15S)-isomers (2, 3, and 5, respectively), were stereoselectively synthesized using a Nozaki-Hiyama-Kishi reaction as a key step. It was also found that a (2R,5S,6S,7R,9R,11S,15S)-isomer (4), corresponding to the absolute configuration of I recently proposed by Sasaki, was not detected during the formation of 5 from a common ketodiol substrate under acid-catalyzed spiroacetalization conditions. This would be attributable to the absence of a macrocyclic framework. (c) 2008 Elsevier Ltd. All rights reserved.