Synthetic studies towards complex diterpenoids. Part 20.1 Total synthesis of the linear abietane o-quinone umbrosone

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Keya Ghosh and Usha Ranjan Ghatak


Abstract

A simple total synthesis of the rearranged linear abietane diterpenoid o-quinone, umbrosone 1, has been accomplished through trans-1,2,3,4,9,9a-hexahydro-1,1-dimethyl-6-methoxyanthracen-10(4aH[hair space])-one 12t.


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