期刊
SCIENCE
卷 341, 期 6148, 页码 878-882出版社
AMER ASSOC ADVANCEMENT SCIENCE
DOI: 10.1126/science.1241606
关键词
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资金
- LEO Pharma
- Carlsberg Foundation
- Danish Council for Independent Research (Technology and Production Sciences)
- Alexander von Humboldt Foundation
Ingenol is a diterpenoid with unique architecture and has derivatives possessing important anticancer activity, including the recently Food and Drug Administration-approved Picato, a first-in-class drug for the treatment of the precancerous skin condition actinic keratosis. Currently, that compound is sourced inefficiently from Euphorbia peplus. Here, we detail an efficient, highly stereocontrolled synthesis of (+)-ingenol proceeding in only 14 steps from inexpensive (+)-3-carene and using a two-phase design. This synthesis will allow for the creation of fully synthetic analogs of bioactive ingenanes to address pharmacological limitations and provides a strategic blueprint for chemical production. These results validate two-phase terpene total synthesis as not only an academic curiosity but also a viable alternative to isolation or bioengineering for the efficient preparation of polyoxygenated terpenoids at the limits of chemical complexity.
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