Synthesis of indenol- and azulenol derivatives via platinum dichloride-catalyzed intramolecular hydroxy- or alkoxycyclization of cyclic dienynes.
Platinum dichloride-catalyzed hydroxy- or alkoxycyclization of cyclohexadienynes gives indenol derivatives, whereas hydroxy- or alkoxycyclization of cycloheptadienynes produces azulenol derivatives. The cyclization reaction proceeds via a cyclopropyl platinacarbene intermediate and allows for the direct stereocontrol of three contiguous stereogenic centers of the fused bicyclic skeletons. The transient reactive intermediate obtained from PtCl2-catalyzed cyclization reaction of a cyclohexadienyndiol can be trapped intramolecularly by a hydroxyl group to afford an oxatricyclo[5.4.0.04,8]undecane ring skeleton with extreme diastereoselectivity.
Yeh
Ming-Chang P
MC
Department of Chemistry, National Taiwan Normal University, 88 Ding-Jou Road, Section 4, Taipei 11677, Taiwan, Republic of China. cheyeh@scc.ntnu.edu.tw
Tsao
Wen-Cheng
WC
Cheng
Sau-Tin
ST
D000480:Alkynes / Q000737:chemistry*; D052176:Azulenes / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D017665:Hydroxyl Radical / Q000737:chemistry*; D007192:Indenes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D017671:Platinum Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D000480:Alkynes; D052176:Azulenes; D007192:Indenes; D017671:Platinum Compounds; D017665:Hydroxyl Radical