Published February 2, 2011
| Supplemental Material
Journal Article
Open
Enantioselective Total Synthesis of (+)-Salvileucalin B
- Creators
-
Levin, Sergiy
- Nani, Roger R.
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Reisman, Sarah E.
Chicago
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Abstract
An enantioselective total synthesis of the diterpenoid natural product (+)-salvileucalin B is reported. Key findings include a copper-catalyzed arene cyclopropanation reaction to provide the unusual norcaradiene core and a reversible retro-Claisen rearrangement of a highly functionalized norcaradiene intermediate.
Additional Information
© 2010 American Chemical Society. Received: November 12, 2010. Article ASAP December 21, 2010. Published In Issue February 02, 2011. We thank Drs. Michael Day and Larry Henling for X-ray crystallographic structural determination and Dr. Scott Virgil for insightful discussions. We thank Prof. Brian Stoltz and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment. HRMS and X-ray crystallographic data were obtained on instruments purchased through awards to the California Institute of Technology by the NSF CRIF program (CHE-0639094, CHE-0541745). Ms. Kendra Joseph is acknowledged for assistance in the preparation of alkyne 9. Financial support from the California Institute of Technology is gratefully acknowledged.Attached Files
Supplemental Material - ja110192b_si_001.pdf
Supplemental Material - ja110192b_si_002.pdf
Supplemental Material - ja110192b_si_003.cif
Files
ja110192b_si_002.pdf
Additional details
- Eprint ID
- 23020
- DOI
- 10.1021/ja110192b
- Resolver ID
- CaltechAUTHORS:20110321-160052573
- NSF
- CHE-0639094
- NSF
- CHE-0541745
- Caltech
- Created
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2011-03-22Created from EPrint's datestamp field
- Updated
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2021-11-09Created from EPrint's last_modified field