Enantioselective imine Michael reaction for the preparation of the (8′ R ,8a′ S )-8,8a′-dimethyl-1′,3′,4′,7′,8′,8a′-hexahydrospiro[1,3-dioxolane-2,2′(6′ H )naphthalen]-6′-one building block. A formal synthesis of (+)-valencenol
Identifieur interne : 001792 ( Main/Exploration ); précédent : 001791; suivant : 001793Enantioselective imine Michael reaction for the preparation of the (8′ R ,8a′ S )-8,8a′-dimethyl-1′,3′,4′,7′,8′,8a′-hexahydrospiro[1,3-dioxolane-2,2′(6′ H )naphthalen]-6′-one building block. A formal synthesis of (+)-valencenol
Auteurs : Gilbert Revial [France] ; Ivan Jabin [France] ; Michaël Redolfi [France] ; Michel Pfau [France]Source :
- Tetrahedron: Asymmetry [ 0957-4166 ] ; 2001.
Abstract
The enantioselective Michael addition of a chiral imine of 4-protected 2-methylcyclohexane-1,4-dione to phenyl crotonate led after cyclization to the corresponding bicyclic lactam. Reductive cleavage of the chiral moiety followed by saponification gave the corresponding keto-acid, which was cyclized to afford a lactone. Belleau–Fujimoto reaction of the lactone then led to the title building block (diastereoselectivity 96:4, e.e. >98%) in 11% overall yield from the starting dione. (8R,8aS)-(+)-8,8a-Dimethyl-3,4,6,7,8,8a-hexahydronaphthalen-2(1H)-one was obtained after reduction of the carbonyl group, acetylation, and reductive cleavage–deprotection (52% overall yield), representing a formal synthesis of (+)-valencenol.
Url:
DOI: 10.1016/S0957-4166(01)00289-0
Affiliations:
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Reductive cleavage of the chiral moiety followed by saponification gave the corresponding keto-acid, which was cyclized to afford a lactone. Belleau–Fujimoto reaction of the lactone then led to the title building block (diastereoselectivity 96:4, e.e. >98%) in 11% overall yield from the starting dione. (8R,8aS)-(+)-8,8a-Dimethyl-3,4,6,7,8,8a-hexahydronaphthalen-2(1H)-one was obtained after reduction of the carbonyl group, acetylation, and reductive cleavage–deprotection (52% overall yield), representing a formal synthesis of (+)-valencenol.</div></front></TEI><affiliations><list><country><li>France</li></country><region><li>Haute-Normandie</li><li>Région Normandie</li><li>Île-de-France</li></region><settlement><li>Le Havre</li><li>Paris</li></settlement><orgName><li>Université du Havre</li></orgName></list><tree><country name="France"><region name="Île-de-France"><name sortKey="Revial, Gilbert" sort="Revial, Gilbert" uniqKey="Revial G" first="Gilbert" last="Revial">Gilbert Revial</name></region><name sortKey="Jabin, Ivan" sort="Jabin, Ivan" uniqKey="Jabin I" first="Ivan" last="Jabin">Ivan Jabin</name><name sortKey="Pfau, Michel" sort="Pfau, Michel" uniqKey="Pfau M" first="Michel" last="Pfau">Michel Pfau</name><name sortKey="Pfau, Michel" sort="Pfau, Michel" uniqKey="Pfau M" first="Michel" last="Pfau">Michel Pfau</name><name sortKey="Redolfi, Michael" sort="Redolfi, Michael" uniqKey="Redolfi M" first="Michaël" last="Redolfi">Michaël Redolfi</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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