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Trinorguaiane sesquiterpenes

H.J. Schafer et al. achieved the formal total synthesis of the trinorguaiane sesquiterpenes ( )-clavukerin and ( )-isoclavukerin by using the Danheiser cyciopentene annulation as the key step. Racemic 4-methylcyclohept-2-en-1-one was reacted with (trimethylsilyl)allene in the presence of 1.7 equivalents of TiCU in dichloromethane at -78 °C to afford a 1 1 mixture of the c/s-fused diastereomers, which were easily separated by HPLC. The diastereomers were then converted to key fragments of earlier total syntheses of the above mentioned natural products. [Pg.125]

The rhodium-cataiyzed intramoiecuiar [5+2] cycioaddition of an allene and vinylcyclopropane was the key step in the asymmetric total synthesis of the trinorguaiane sesquiterpene (+)-dictamnol by P.A. Wender and co-workers.The cyclization precursor allene-cyclopropane was assembled starting from commercially available cyclopropane-carbaldehyde. Using the HWE oiefination, the Weinreb s amide moiety was installed and subsequently reacted with a primary alkyllithium that was generated via lithium-halogen exchange. [Pg.479]

Friese, J. C., Krause, S., Schafer, H. J. Formal total synthesis of the trinorguaiane sesquiterpenes ( )-clavukerin Aand ( )-isoclavukerin. Tetrahedron Lett. 2002, 43, 2683-2685. [Pg.570]

Honda, T., Ishige, H., and Nagase, H. (1994) Chiral synthesis of a trinorguaiane sesquiterpene, davukerin A. J. Chem. Soc. Perkin Trans. I, 3305-3310. [Pg.1409]


See other pages where Trinorguaiane sesquiterpenes is mentioned: [Pg.1409]    [Pg.1409]   
See also in sourсe #XX -- [ Pg.125 ]




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