Synthesis of (+/-)-thiohalenaquinone by iterative metalations of thiophene.
The synthesis of a thiophene-containing analogue of halenaquinone was realized. Key steps include an alkynyl ketone-benzocyclobutane Diels-Alder reaction to construct the C,D-ring naphthalene subunit, a Heck cyclization to form the quaternary carbon, and a ring closing metathesis to add the A-ring.
Wakefield
Bryan
B
Department of Chemistry and Center for Chemical Methodologies & Library Development, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA.
Halter
Robert J
RJ
Wipf
Peter
P
D000818:Animals; D003500:Cyclization; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry; D011809:Quinones / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013876:Thiophenes / Q000737:chemistry*
D011809:Quinones; D013876:Thiophenes; C522303:thiohalenaquinone; C430084:halenaquinone