Total synthesis of (+/-)-gleenol and (+/-)-axenol via a functionalized spiro[4.5]decane.
Total synthesis of (+/-)-gleenol and (+/-)-axenol via a functionalized spiro[4.5]decane.
复制标题
通过功能化螺[4.5]癸烷全合成(i-)-gleenol和(i-)-axenol。
DOI：
10.1248/cpb.55.1606
复制
发表时间：
2007
影响因子：
1.7
通讯作者：
Susumu Kobayashi
中科院分区：
文献类型：
--
作者：
Atsuo Nakazaki;T. Era;Susumu Kobayashi
生物学上重要的 axane 倍半萜、gleenol (1) 和 axenol (2) 的全合成是通过容易获得的螺[4.5]癸烷完成的。 1和2合成的关键特征包括克莱森重排，以优异的收率提供多官能化螺[4.5]癸烷4作为单一非对映异构体，通过烯酮二硫缩醛安装C7异丙基而不是直接烷基化，以及在Birch条件下酮的非对映选择性还原。
Total synthesis of the biologically important axane sesquiterpenes, gleenol (1) and axenol (2), was accomplished through a readily available spiro[4.5]decane. The key features of the synthesis of 1 and 2 include Claisen rearrangement to afford the multi-functionalized spiro[4.5]decane 4 as a single diastereomer in excellent yield, installation of the C7 isopropyl group via ketene dithioacetal instead of direct alkylation and a diastereoselective reduction of ketone under the Birch conditions.