Photocyclization-fragmentation route to di- and triquinanes: Stereocontrolled asymmetric synthesis of (-)-isocomene
摘要：
We recently reported a general approach to the di- and triquinane frameworks. The strategy takes advantage of two powerful reactions to build the molecular complexity, a Diels-Alder reaction to construct a norbornane, and a Paterno-Buchi reaction to form a latent diquinane. The key step in the strategy is a reductive fragmentation reaction which liberates the quinane skeleton. This presentation will focus on the successful implementation of this strategy to the first controlled asymmetric synthesis of (-)-isocomene. The chirality of the natural product is derived from a highly scalemic norbornene ester that is readily available via the Helmchen Diels-Alder reaction. Subsequent elaboration provides a strained ketoalkene. Selective fragmentation of strategic bonds and further transformations afford the natural product in optically pure form, in good overall yield. Recent results aimed at altering the ''normal'' course of the reductive fragmentation will also be described.
展开
关键词：
Formal total synthesis Olefin synthesis (+/-)-isocomene Isocomene Stereochemistry Sesquiterpenes Rearrangements
DOI：
10.1351/pac199668030675
被引量：
年份：
1996
De Gruyter
(全网免费下载)
De Gruyter
国家科技图书文献中心
(权威机构)
掌桥科研
doi.org
查看更多
dx.doi.org
ResearchGate
ResearchGate
(全网免费下载)
EBSCO
iupac.org
(全网免费下载)
media.iupac.org
(全网免费下载)
moureu.iupac.org
(全网免费下载)
iupac.org
d.scholar.cnki.net
list.iupac.org
(全网免费下载)
old.iupac.org
(全网免费下载)
学术范
(全网免费下载)
iupac.org
(全网免费下载)
学术范
onAcademic
De Gruyter
(全网免费下载)
ResearchGate
(全网免费下载)
iupac.org
(全网免费下载)
list.iupac.org
(全网免费下载)
moureu.iupac.org
(全网免费下载)
media.iupac.org
(全网免费下载)
old.iupac.org
(全网免费下载)
iupac.org
(全网免费下载)
学术范
(全网免费下载)
通过文献互助平台发起求助，成功后即可免费获取论文全文。
相似文献
参考文献
引证文献
辅助模式
引用
文献可以批量引用啦~
欢迎点我试用！
