Enantioselective construction of the tricyclic core of curcusones A-D via a cross-electrophile coupling approach

Herein we report our recent progress toward the enantioselective total synthesis of the diterpenoid natural products curcusones A-D by means of complementary Stetter annulation or ring-closing metathesis (RCM) disconnections. Using the latter approach, we have achieved the concise construction of th...

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Bibliographic Details
Published inChemical science (Cambridge) Vol. 10; no. 45; pp. 10562 - 10565
Main Authors Wright, Austin C., Stoltz, Brian M.
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 07.12.2019
Royal Society of Chemistry
Subjects
Chemical reactions
Chemistry
Chemistry, Multidisciplinary
Coupling
Crystallography
Enantiomers
Infrared spectroscopy
Metathesis
Natural products
NMR
Nuclear magnetic resonance
Physical Sciences
Science & Technology
Synthesis
DITERPENES
KETONES
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Summary:Herein we report our recent progress toward the enantioselective total synthesis of the diterpenoid natural products curcusones A-D by means of complementary Stetter annulation or ring-closing metathesis (RCM) disconnections. Using the latter approach, we have achieved the concise construction of the 5-7-6 carbocyclic core embedded in each member of the curcusone family. Essential to this route is the use of a cross-electrophile coupling strategy, which has not previously been harnessed in the context of natural product synthesis.
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ISSN:2041-6520
2041-6539
DOI:10.1039/c9sc04127c