Published August 10, 2016
| Version Supplemental Material
Journal Article
Open
Enantioselective Total Synthesis of (+)-Psiguadial B
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1.
California Institute of Technology
Abstract
The first enantioselective total synthesis of the cytotoxic natural product (+)-psiguadial B is reported. Key features of the synthesis include (1) the enantioselective preparation of a key cyclobutane intermediate by a tandem Wolff rearrangement/asymmetric ketene addition, (2) a directed C(sp^3)–H alkenylation reaction to strategically forge the C1–C2 bond, and (3) a ring-closing metathesis to build the bridging bicyclo[4.3.1]decane terpene framework.
Additional Information
© 2016 American Chemical Society. Received: July 13, 2016. Published: July 24, 2016. Prof. Greg Fu is gratefully acknowledged for insightful discussions. We thank Dr. Allen Oliver and Dr. Nathan Schley for X-ray crystallographic structure determination, Dr. David VanderVelde for assistance with NMR structure determination, Dr. Scott Virgil and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment, and Materia, Inc. for a donation of HG-II catalyst. Fellowship support was provided by the NSF (L.M.C., Grant DGE-1144469) and SNF (L.W., Grant PBZHP2-147311). S.E.R. is an American Cancer Society Research Scholar and a Heritage Medical Research Foundation Investigator. Financial support from the California Institute of Technology, the NSF (CHE 1057143), the American Cancer Society, the Research Corporation Cottrell Scholars Program, and DuPont is gratefully acknowledged.Attached Files
Supplemental Material - ja6b07229_si_001.cif
Supplemental Material - ja6b07229_si_003.pdf
Files
ja6b07229_si_003.pdf
Additional details
Identifiers
- Eprint ID
- 69632
- Resolver ID
- CaltechAUTHORS:20160815-142455841
Related works
- Describes
- http://pubs.acs.org/doi/suppl/10.1021/jacs.6b07229 (URL)
Funding
- NSF Graduate Research Fellowship
- DGE-1144469
- Swiss National Fund (SNF)
- PBZHP2-147311
- NSF
- CHE-1057143
- American Cancer Society
- Cottrell Scholar of Research Corporation
- Heritage Medical Research Foundation
- Caltech
- DuPont
Dates
- Created
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2016-08-15Created from EPrint's datestamp field
- Updated
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2021-11-11Created from EPrint's last_modified field
Caltech Custom Metadata
- Caltech groups
- Heritage Medical Research Institute