Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 138, Issue 31, Pages 9803-9806Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b07229
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Funding
- NSF [DGE-1144469, CHE 1057143]
- SNF [PBZHP2-147311]
- California Institute of Technology
- American Cancer Society
- Research Corporation Cottrell Scholars Program
- DuPont
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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 Cl-C2 bond, and (3) a ring-closing metathesis to build the bridging bicyclo[4.3.1]decane terpene framework.
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