Formal Total Synthesis of Pericoannosin A

A concise formal total synthesis of pericoannosin A, by the synthesis of an advanced intermediate of pericoannosin A, was achieved in eight steps from commercially available isoprene in a 21.7% overall yield. Key transformations for this expedited route include an enantioselective organocatalytic Di...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 84; no. 18; pp. 12187 - 12191
Main Authors Fulton, Mark G, Bertron, Jeanette L, Reed, Carson W, Lindsley, Craig W
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 20.09.2019
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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Summary:A concise formal total synthesis of pericoannosin A, by the synthesis of an advanced intermediate of pericoannosin A, was achieved in eight steps from commercially available isoprene in a 21.7% overall yield. Key transformations for this expedited route include an enantioselective organocatalytic Diels–Alder reaction to construct the C ring, a diastereoselective reduction (under Felkin–Ahn control), and a hydroboration/oxidation sequence for chain homologation. This work represents the second synthetic effort toward pericoannosin A, the only reported natural product based on a hexahydro-1H-isochromen-5-isobutylpyrrolidin-2-one core.
Bibliography:ObjectType-Article-1
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content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b01846