Total synthesis of (±)-heliannuol C and E via aromatic Claisen rearrangement

(±)-Heliannuols C and E were synthesized from a common epoxide intermediate in only seven steps overall from 2-methylanisole. The total synthesis of heliannuol C and E from a common intermediate are described. Key steps in the synthesis include a regioselective aromatic Claisen rearrangement to inst...

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Bibliographic Details
Published inTetrahedron letters Vol. 46; no. 14; pp. 2457 - 2460
Main Authors Vyvyan, James R., Oaksmith, Jennifer M., Parks, Bevin W., Peterson, Elaine M.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 04.04.2005
Elsevier
Subjects
Allelopathy
Biomimetic reactions
Chemistry
Chemistry, Organic
Epoxides
Herbicides
Oxygen heterocycles
Physical Sciences
Science & Technology
Biomimetic reactions
Allelopathy
Herbicides
Oxygen heterocycles
Epoxides
ALLELOCHEMICALS
NATURAL-PRODUCTS
HELIANNUOL-E
biomimetic reactions
BIOACTIVE SESQUITERPENE
CLEAVAGE
oxygen heterocycles
allelopathy
DEMETHYLATION
GENERATION
epoxides
ARYL ALKYL ETHERS
ENANTIOSELECTIVE TOTAL-SYNTHESIS
herbicides
EFFICIENT PROTOCOL
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Summary:(±)-Heliannuols C and E were synthesized from a common epoxide intermediate in only seven steps overall from 2-methylanisole. The total synthesis of heliannuol C and E from a common intermediate are described. Key steps in the synthesis include a regioselective aromatic Claisen rearrangement to install the (1-vinyl)-4-methyl-3-pentenyl substituent and regioselective biomimetic 7- endo and 6- exo phenol epoxide cyclizations to form the cyclic ether moieties.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2005.02.053