Total Synthesis of Hyperforin

A 10-step total synthesis of the polycyclic polyprenylated acylphloroglucinol (PPAP) natural product hyperforin from 2-methylcyclopent-2-en-1-one is reported. This route was enabled by a diketene annulation reaction and an oxidative ring expansion strategy designed to complement the presumed biosynt...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 137; no. 33; pp. 10516 - 10519
Main Authors Ting, Chi P, Maimone, Thomas J
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 26.08.2015
Amer Chemical Soc
Subjects
Chemistry
Chemistry Techniques, Synthetic
Chemistry, Multidisciplinary
Oxidation-Reduction
Phloroglucinol - analogs & derivatives
Phloroglucinol - chemical synthesis
Phloroglucinol - chemistry
Physical Sciences
Science & Technology
Terpenes - chemical synthesis
Terpenes - chemistry
ALKYLATIVE DEAROMATIZATION-ANNULATION
BIOMIMETIC TOTAL-SYNTHESIS
FORMAL SYNTHESIS
POLYCYCLIC POLYPRENYLATED ACYLPHLOROGLUCINOLS
STEREOSELECTIVE TOTAL-SYNTHESIS
PHLOROGLUCIN NATURAL-PRODUCTS
ASYMMETRIC TOTAL-SYNTHESIS
GARSUBELLIN-A
GRIGNARD-REAGENTS
CONJUGATE ADDITION
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Summary:A 10-step total synthesis of the polycyclic polyprenylated acylphloroglucinol (PPAP) natural product hyperforin from 2-methylcyclopent-2-en-1-one is reported. This route was enabled by a diketene annulation reaction and an oxidative ring expansion strategy designed to complement the presumed biosynthesis of this complex meroterpene. The described work enables the preparation of a highly substituted bicyclo[3.3.1]­nonane-1,3,5-trione motif in only six steps and thus serves as a platform for the construction of easily synthesized, highly diverse PPAPs modifiable at every position.
Bibliography:NIH RePORTER
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ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.5b06939