Biomimet1c cyclization of 4β, 5α-epoxy-6β-acetoxy-trans-germacr-1(10)-ene to form cis-( 1β-h ; 5β-h)-guaianes

Add time:09/05/2019    Source:sciencedirect.com

A new 4β,5α-epoxy-6β-acetoxy-trans-germacr-l(10)-ene has been isolated from Sideritis varoi subsp. cuatrecasasii. The product has been subjected to several biomimetic cyclizations which have rendered cis-(1β-H,5β-H)-guaianes. One of these guaianes presents the same structure as a product also present in an extract of this plant.Chemical structure of guaianes have been established by 1H-NMR, 13c NMR, ORD experiences and chemical correlations.The stereoespecificity of the cyclization is explained according to a conformation in which the 14 and 15 methyl groups are syn.

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