Total Synthesis of (−)-Himandrine
We describe the first total synthesis of (−)-himandrine, a member of the class II galbulimima alkaloids. Noteworthy features of this chemistry include a diastereoselective Diels−Alder reaction in the rapid synthesis of the tricycle ABC-ring system in an enantiomerically enriched form, the use of a f...
| Main Authors: | , , |
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| Other Authors: | |
| Format: | Article |
| Language: | en_US |
| Published: |
American Chemical Society
2012
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| Online Access: | http://hdl.handle.net/1721.1/71907 https://orcid.org/0000-0003-3080-1063 |
| Summary: | We describe the first total synthesis of (−)-himandrine, a member of the class II galbulimima alkaloids. Noteworthy features of this chemistry include a diastereoselective Diels−Alder reaction in the rapid synthesis of the tricycle ABC-ring system in an enantiomerically enriched form, the use of a formal [3+3] annulation strategy to secure the CDE-ring system with complete diastereoselection, and successful implementation of our biogenetically inspired oxidative spirocyclization of an advanced intermediate. The successful and direct late-stage formation of the F-ring in the hexacyclic core of himandrine drew on the power of biogenetic considerations and fully utilized the inherent chemistry of a plausible biosynthetic intermediate. |
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