Facile total synthesis of (±)-α-herbertenol, (±)-α-cuparenone and (±)-HM-1 methyl ether involving alkylation of hindered esters

The total syntheses of (±)-α-herbertenol 1, (±)-α-cuparenone 4 and (±)-HM-1 methyl ether 3 have been successfully accomplished involving α,α-dimethylation of the esters 8a, 17 and 8b respectively as key steps. α,α-Dimethylation of the esters 1,3 and 5 furnished the esters 2,4 and 6 which were conver...

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Bibliographic Details
Published inTetrahedron letters Vol. 40; no. 25; pp. 4733 - 4734
Main Authors Pal, Ashutosh, Gupta, Pranab Dutta, Roy, Arnab, Mukherjee, Debabrata
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 18.06.1999
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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Summary:The total syntheses of (±)-α-herbertenol 1, (±)-α-cuparenone 4 and (±)-HM-1 methyl ether 3 have been successfully accomplished involving α,α-dimethylation of the esters 8a, 17 and 8b respectively as key steps. α,α-Dimethylation of the esters 1,3 and 5 furnished the esters 2,4 and 6 which were converted into (±)-α-herbertenol 7, (±)-α-cuparenone 8 and (±)-HM-1 methyl ether 9 respectively.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(99)00835-7