A new route to benzo[4,5]cyclohepta[1,2-b]naphthalenes: synthesis of radermachol.
[formula: see text] Condensation of 3-phenylsulfonyl-1,3-isobenzofuranone (3) with benzocyclohept-6,7-en-5-ones such as 4 and 15 provides a straightforward, general method for synthesis of functionalized benzo[4,5]cyclohepta[1,2-b]naphthalenes (e.g., 5 and 16). This finding was used to achieve a brief and efficient preparation of 6,7-benzo-3,4-(1,4-dimethoxy-2,3-naphtho)-1,5-dioxosuberane (2), an established intermediate to the naturally occurring red pigment radermachol (1).
Hauser
F M
FM
Department of Chemistry, University at Albany, State University of New York 12222, USA.
Yin
H
H
D003508:Cycloheptanes / Q000138:chemical synthesis*; D009281:Naphthalenes / Q000138:chemical synthesis*
D003508:Cycloheptanes; D009281:Naphthalenes; C408866:radermachol