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Rapid Construction of the Aza-Propellane Core of Acutumine via a Photochemical [2 + 2] Cycloaddition Reaction

Navarro, Raul and Reisman, Sarah E. (2012) Rapid Construction of the Aza-Propellane Core of Acutumine via a Photochemical [2 + 2] Cycloaddition Reaction. Organic Letters, 14 (17). pp. 4354-4357. ISSN 1523-7060. PMCID PMC3445413. doi:10.1021/ol3017963. https://resolver.caltech.edu/CaltechAUTHORS:20121011-093625947

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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.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ol3017963DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ol3017963PublisherArticle
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3445413/PubMed CentralArticle
ORCID:
AuthorORCID
Reisman, Sarah E.0000-0001-8244-9300
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.
Funders:
Funding AgencyGrant Number
Bill and Melinda Gates FoundationUNSPECIFIED
NIH Predoctoral FellowshipF31GM098025
NSFCHE-0639094
NSFCHE-0541745
CaltechUNSPECIFIED
NSFCHE-1057143
Issue or Number:17
PubMed Central ID:PMC3445413
DOI:10.1021/ol3017963
Record Number:CaltechAUTHORS:20121011-093625947
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20121011-093625947
Official Citation:Rapid Construction of the Aza-Propellane Core of Acutumine via a Photochemical [2 + 2] Cycloaddition Reaction Raul Navarro and Sarah E. Reisman Organic Letters201214 (17), 4354-4357
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:34842
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:11 Oct 2012 18:54
Last Modified:09 Nov 2021 23:11

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