Efficient formal synthesis of (±)-hyphodermin B

Henderson, Luke C., Loughlin, Wendy A., Jenkins, Ian D., Healy, Peter C. and Campitelli, Marc R. 2006, Efficient formal synthesis of (±)-hyphodermin B, Journal of organic chemistry, vol. 71, no. 6, pp. 2384-2388, doi: 10.1021/jo052485l.

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Title Efficient formal synthesis of (±)-hyphodermin B
Author(s) Henderson, Luke C.ORCID iD for Henderson, Luke C. orcid.org/0000-0002-4244-2056
Loughlin, Wendy A.
Jenkins, Ian D.
Healy, Peter C.
Campitelli, Marc R.
Journal name Journal of organic chemistry
Volume number 71
Issue number 6
Start page 2384
End page 2388
Publisher American Chemical Society
Place of publication Washington, D.C.
Publication date 2006-03-17
ISSN 0022-3263
Summary An efficient formal synthesis of hyphodermin B 1, a metabolite of Hyphoderma radula, has been completed in 15% overall yield. The tricyclic carbon skeleton 3 was rapidly assembled from a novel vinyl enone via a Diels−Alder reaction, followed by dehydrogenation and anhydride formation. Selective reduction of anhydride 3 with LiAlH(t-BuO)3 gave hyphodermin B 1 in 99% yield. The structure of hyphodermin B 1 was confirmed by X-ray crystallographic analysis. The anhydride 3, bearing a γ-carbonyl group, displayed unexpected reactivity with the anhydride carbonyl closest to the γ-ketone being the most electrophilic site. This was confirmed by HF/6-31G* calculations. In the presence of base, 3 underwent a rearrangement to the novel lactone 16.
Language eng
DOI 10.1021/jo052485l
Field of Research 030503 Organic Chemical Synthesis
HERDC Research category C1.1 Refereed article in a scholarly journal
Copyright notice ©2006, American Chemical Society
Persistent URL http://hdl.handle.net/10536/DRO/DU:30028582

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