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Cyclopropane compatibility with oxidative carbocation formation: total synthesis of clavosolide A.

Organic letters (2012-10-26)
GuangRong Peh, Paul E Floreancig
ABSTRACT

Cyclopropane-substituted allylic ethers react with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone to form oxocarbenium ions with no competitive ring cleavage. This reaction can be used for the preparation of cyclopropane-substituted tetrahydropyrans. The protocol was used as a key step in the total synthesis of the sponge-derived macrolide clavosolide A.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
p-Benzoquinone, reagent grade, ≥98%
Supelco
1,4-Benzoquinone, Pharmaceutical Secondary Standard; Certified Reference Material
Supelco
p-Benzoquinone, for spectrophotometric det. of amines, ≥99.5% (HPLC)
Sigma-Aldrich
Cyclopropane, ≥99%