Biomimetic Synthesis of Isorosmanol and Przewalskin A.

Przewalskin A, a novel C23 terpenoid with anti-HIV-1 activity from Salvia przewalskii Maxim, was formed in 10 steps via isorosmanol from (+)-carnosic acid. The synthetic strategy was inspired primarily by the biogenetic hypothesis and was enabled by epoxidation, epoxide ring opening, and lactonization in one pot to prepare the 11,12-dimethoxy isorosmanol, and bismuthonium ylide-induced ring expansion of o-quinone to construct the 2-acyl-3-hydroxytropone.