We describe an alkylative dearomatization/acid-mediated adamantane annulation sequence that allows facile access to type A polyprenylated acylphloroglucinol natural products including plukenetione A. Introduction of the 2-methyl-1-propenyl moiety was achieved via stereodivergent S(N)2 and S(N)1 cyclizations of allylic alcohol substrates.
Pathak, V. P.; Saini, T. R.; Khanna, R.N., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1984, vol. 23, # 6, p. 571 - 572