Published September 28, 2011
| Supplemental Material
Journal Article
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A Concise Total Synthesis of (--)-Maoecrystal Z
Chicago
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Abstract
The first total synthesis of (--)-maoecrystal Z is described. The key steps of the synthesis include a diastereoselective Ti^(III)-mediated reductive epoxide coupling reaction and a diastereoselective Sm^(II)-mediated reductive cascade cyclization reaction. These transformations enabled the preparation of (--)-maoecrystal Z in only 12 steps from (--)-γ-cyclogeraniol.
Additional Information
© 2011 American Chemical Society. Received: August 4, 2011. Publication Date (Web): August 30, 2011. We thank Dr. Michael Day and Mr. Larry Henling for X-ray crystallographic structure determination and Dr. David Vander-Velde for assistance with NMR structure determination. We thank Prof. Brian Stoltz and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment and Dr. Scott Virgil for insightful discussions. The Bruker KAPPA APEXII X-ray diffractometer was purchased through an award to the California Institute of Technology by the NSF CRIF program (CHE-0639094). Financial support from the California Institute of Technology is gratefully acknowledged.Attached Files
Supplemental Material - ja2073356_si_001.pdf
Supplemental Material - ja2073356_si_002.pdf
Supplemental Material - ja2073356_si_003.cif
Files
ja2073356_si_001.pdf
Additional details
- Eprint ID
- 27507
- DOI
- 10.1021/ja2073356
- Resolver ID
- CaltechAUTHORS:20111031-072905834
- NSF
- CHE-0639094
- Caltech
- Created
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2011-10-31Created from EPrint's datestamp field
- Updated
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2021-11-09Created from EPrint's last_modified field