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Total Synthesis of (+)‐Strongylin A, a Rearranged Sesquiterpenoid Hydroquinone from a Marine Sponge
Author(s) -
Kamishima Takaaki,
Kikuchi Takuya,
Katoh Tadashi
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300438
Subject(s) - stereocenter , decalin , total synthesis , chemistry , natural product , moiety , stereochemistry , hydroquinone , sponge , derivative (finance) , yield (engineering) , absolute configuration , enantioselective synthesis , organic chemistry , catalysis , botany , materials science , metallurgy , financial economics , economics , biology
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 · Et 2 O‐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.