Progress toward the Enantioselective Synthesis of Curcusones A–D via a Divinylcyclopropane Rearrangement Strategy

We report our iterative efforts toward the divergent total syntheses of curcusones A–D via Suzuki coupling, intramolecular cyclopropanation, and a key divinylcyclopropane rearrangement. Progress of our synthesis was repeatedly challenged by the highly substrate-dependent cyclopropanation step, which...

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Published inOrganic letters Vol. 21; no. 23; pp. 9658 - 9662
Main Authors Wright, Austin C, Lee, Chung Whan, Stoltz, Brian M
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.12.2019
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CORE
RHAMNOFOLANE DITERPENES
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Summary:We report our iterative efforts toward the divergent total syntheses of curcusones A–D via Suzuki coupling, intramolecular cyclopropanation, and a key divinylcyclopropane rearrangement. Progress of our synthesis was repeatedly challenged by the highly substrate-dependent cyclopropanation step, which we could ultimately overcome by judicious choice of substituents on the six-membered ring fragment.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b03829