Published September 7, 2012
| Accepted Version + Supplemental Material + Published
Journal Article
Open
Rapid Construction of the Aza-Propellane Core of Acutumine via a Photochemical [2 + 2] Cycloaddition Reaction
- Creators
- Navarro, Raul
-
Reisman, Sarah E.
Abstract
Synthetic efforts toward the chlorinated aza-propellane alkaloid acutumine (1) are described. The key vicinal quaternary centers were constructed by a photochemical [2 + 2] cycloaddition reaction of a furanyl-tetrahydroindolone. Dihydroxylation of the [2 + 2] product enabled a tandem retro-aldol/intramolecular ketalization reaction, which revealed the aza-propellane core of 1 while generating an unusual, caged, pentacyclic hemiketal product.
Additional Information
© 2012 American Chemical Society. Received June 29, 2012. Article ASAP August 14, 2012. Published In Issue September 07, 2012. We thank several of our colleagues at the California Institute of Technology: Dr. Michael Day and Mr. Larry Henling for X-ray crystallographic structural determination, Dr. David Vander Velde for assistance with NMR structural determination, and Prof. Brian Stoltz, Dr. Scott Virgil, and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment. Fellowship support was provided by the Gates Millennium Scholars Program (R.N.) and the NIH (R.N., F31GM098025). 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). Financial support from the California Institute of Technology and the NSF (CAREER-1057143) is gratefully acknowledged.Attached Files
Published - ol3017963.pdf
Accepted Version - nihms400826.pdf
Supplemental Material - ol3017963_si_001.pdf
Supplemental Material - ol3017963_si_002.pdf
Supplemental Material - ol3017963_si_003.cif
Supplemental Material - ol3017963_si_004.cif
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ol3017963.pdf
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Additional details
- PMCID
- PMC3445413
- Eprint ID
- 34842
- Resolver ID
- CaltechAUTHORS:20121011-093625947
- Bill and Melinda Gates Foundation
- F31GM098025
- NIH Predoctoral Fellowship
- CHE-0639094
- NSF
- CHE-0541745
- NSF
- Caltech
- CHE-1057143
- NSF
- Created
-
2012-10-11Created from EPrint's datestamp field
- Updated
-
2021-11-09Created from EPrint's last_modified field