- Enantiospecific first total synthesis of cucumin-H
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Enantiospecific first total synthesis of the linear triquinane sesquiterpene cucumin-H has been described. (R)-Limonene has been employed as the chiral starting material and a combination of Claisen rearrangement, intramolecular cyclopropanation and Nazar
- Srikrishna,Dethe, Dattatraya H.
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p. 1092 - 1106
(2011/10/05)
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- Synthesis and rearrangement of [1,1′-bicyclobutyl]-1-ols and spiro[3.4]octan-5-ols: A general access to bicyclo[3.3.0]octenes (hexahydropentalenes)
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Several new Grignard reagents based on substituted cyclobutanes have been generated and added to cyclobutanones to yield mono- to trimethylated [1,1′-bicyclobutyl]-1-ols. Mono- to trimethylated spiro[3.4]octan-5-ols have been prepared from the parent ketone via alkylation and/or addition reactions. Upon treatment with acid, all [1,1′-bicyclobutyl]-1-ols and spiro[3.4]octan-5-ols rearrange to yield a single bicyclo[3.3.0]octene. Mono- to trimethylated [1,1′-bicyclobutyl]-1-ols and spiro[3.4]octan-5-ols have been synthesized and rearranged to yield a single bicyclo[3.3.0]octene in each case. Examples are 42, 43, 44 and 45.
- Mandelt, Klaus,Meyer-Wilmes, Imelda,Fitjer, Lutz
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p. 11587 - 11595
(2007/10/03)
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- Enantiospecific first total synthesis and assignment of absolute configuration of the sesquiterpene (-)-cucumin H
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(Matrix presented) The first total synthesis of the sesquiterpene (-)-cucumin H, a linear triquinane isolated from Macrocystidia cucumis, has been accomplished starting from (R)-limonene employing two different cyclopentannulation methodologies, which in
- Srikrishna,Dethe, Dattatraya H.
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p. 2295 - 2298
(2007/10/03)
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