Synthesis of diindeno-fused 4H-cyclopenta[def]phenanthren-4-ones and related compounds via benzannulated enediynyl propargylic alcohols.
[reaction: see text] Treatment of propargylic diols 5-7 with thionyl chloride promoted a cascade sequence of reactions leading to dichlorides 10-12 and, after reduction with tributyltin hydride, the diindeno-fused 4H-cyclopenta[def]phenanthrenes 13-15 in a single operation. Hydrolysis of 13 and 14 furnished 4H-cyclopenta[def]phenanthren-4-ones 16 and 17, respectively. Air oxidation of an alkaline solution of dichloride 11 produced diketone 18.
Han
Xiaoqing
X
C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506-6045, USA.
Zhang
Yanzhong
Y
Wang
Kung K
KK
D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry*; D006067:Gonanes / Q000138:chemical synthesis*; D007659:Ketones / Q000138:chemical synthesis*; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000138:chemical synthesis*; D020005:Propanols / Q000737:chemistry*
D000438:Alcohols; D000480:Alkynes; D006067:Gonanes; D007659:Ketones; D011083:Polycyclic Compounds; D020005:Propanols; C013460:cyclopentaphenanthrene; C028255:propargyl alcohol