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Enantioselective Total Synthesis of Dysidavarone A, a Novel Sesquiterpenoid Quinone from the Marine Sponge Dysidea avara
Author(s) -
Fukui Yurie,
Narita Koichi,
Katoh Tadashi
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201304809
Subject(s) - sponge , enantioselective synthesis , quinone , botany , stereochemistry , biology , chemistry , organic chemistry , catalysis
Dysidavarone A, a structurally unprecedented sesquiterpenoid quinone, was synthesized in 30 % overall yield in a longest liner sequence of 13 steps from commercially available o ‐vanillin. A highly strained and bridged eight‐membered carbocyclic core was established by the C7C21 carbon bond formation through a copper enolate mediated Michael addition to the internal quinone ring.