Synthesis of the naphthalene portion of the rubromycins.
[reaction: see text]. A synthesis of a reduced version of the naphthazarin found in the rubromycin class of natural products is reported. The naphthalene ring system is formed via a Dötz reaction with a symmetrical alkyne. Differentiation between the C1' and C3' groups of the Dötz adduct is achieved by selective oxidation since the two methylene groups possess different oxidation potentials.
Xie
X
X
Department of Chemistry, Roy and Diana Vagelos Laboratories, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA.
Kozlowski
M C
MC
D009281:Naphthalenes / Q000737:chemistry*; D010084:Oxidation-Reduction; D011809:Quinones / Q000138:chemical synthesis* / Q000737:chemistry
D009281:Naphthalenes; D011809:Quinones; C031721:naphthalene