Total Synthesis of (+)-Pestalofone A and (+)-Iso-A82775C

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We describe the total synthesis of epoxyquinoid natural products (+)-pestalofone A and (+)-iso-A82775C. The synthesis of (+)-16-oxo-iso-A82775C, the putative biosynthetic precursor of pestalofone C, is also presented. The allene moiety present in (+)-iso-A82775C and (+)-16-oxo-iso-A82775C was constructed from the ketodiene-yne group via a biosynthetically relevant sequence involving a conjugate reduction and a basecatalyzed tautomerization. Attempted Diels−Alder reaction-based dimerizations of (+)-16-oxo-iso-A82775C and (+)-iso-A82775C toward pestalofones B and C are also described.
Publisher
AMER CHEMICAL SOC
Issue Date
2020-05
Language
English
Article Type
Article
Citation

JOURNAL OF ORGANIC CHEMISTRY, v.85, no.10, pp.6815 - 6821

ISSN
0022-3263
DOI
10.1021/acs.joc.0c00770
URI
http://hdl.handle.net/10203/274219
Appears in Collection
CH-Journal Papers(저널논문)
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