Total Synthesis of (−)-Himandrine
Name
Movassaghi_Total Synthesis.pdf
Size
1.4 MB
Format
Adobe PDF
Checksum (MD5)
db2f405c8466497087b377dad11dbe9c
Author(s)
Movassaghi, Mohammad
Tjandra, Meiliana
Qi, Jun
Date Issued
June 2009
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society
Citation
Movassaghi, Mohammad, Meiliana Tjandra, and Jun Qi. “Total Synthesis of (−)-Himandrine.” Journal of the American Chemical Society 131.28 (2009): 9648-9650.
Version
Author's final manuscript
Abstract
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.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
Terms of Use
Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use.
Persistent DSpace Link
DOI of Published Version
https://doi.org/10.1021/ja903790y
