136978-48-8Relevant articles and documents
Total synthesis of (+)-strongylin A, a rearranged sesquiterpenoid hydroquinone from a marine sponge
Kamishima, Takaaki,Kikuchi, Takuya,Katoh, Tadashi
, p. 4558 - 4563 (2013)
A biologically attractive and structurally unique marine natural product, (+)-strongylin A (1), was synthesized for the first time by starting from a known trans-decalone derivative (19 % overall yield in 11 steps). The synthetic method involved the following key steps: (i) stereocontrolled hydrogenation of an exo-olefinic decalin to install the C8 stereogenic centre present in the required decalin segment; (ii) coupling of the decalin segment with an aromatic moiety to assemble the desired carbon skeleton; and (iii) sequential BF 3·Et2O-induced dehydroxylation/rearrangement/ cyclization of a decalin tertiary alcohol to directly produce target compound 1. This total synthesis has established the absolute configuration of the natural product. (+)-Strongylin A has been synthesized for the first time by starting from (+)-5-methyl-Wieland-Miescher ketone (16 % overall yield in 14 steps). The characteristic tetracyclic core structure was constructed in a domino dehydroxylation/rearrangement/cyclization reaction. Copyright
