Enantiospecific synthesis of the tricyclic core structure of lippifolianes

Tetrahedron Asymmetry

Volumn 21, Issue 6, 2010, Pages 719-724

  Srikrishna, Adusumilli ^a   Ramesh Babu, R ^a   Beeraiah, Baire ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; DITERPENE; LIPPIFOLIANE; SESQUITERPENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CIRCULAR DICHROISM; ENANTIOSELECTIVITY; PRIORITY JOURNAL; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 77953132126     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2010.04.001     Document Type: Article

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33. Although the exact origin of the high regioselectivity in the insertion reaction is not very clear, it is probably due to the presence of all three substituents on the cyclohexene ring in pseudoequitorial orientation, and for the insertion of the rhodium carbenoid in the cyclohexene olefin they need to be in high energy conformation, where all the three substituents need to be in axial orientation. Similarly, origin of the stereoselectivity is also not very clear, but probably due to the reaction of the more preferred rotamer i, over iii, of the rhodium carbenoid derived from the α-diazo-β-ketoester 26. The corresponding rhodium carbenoid ii derived from the α-diazoketone 22, being less stable and more reactive than i, exhibited lower selectivity.{A figure is presented}