Total Synthesis of (+)‐Strongylin A, a Rearranged Sesquiterpenoid Hydroquinone from a Marine Sponge | Zendy

Kamishima Takaaki | Zendy; Kikuchi Takuya | Zendy; Katoh Tadashi | Zendy

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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.

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