Silicon-directed oxa-Pictet-Spengler cyclization and an unusual dimerization of 2-trimethylsilanyl tryptophols.
The tetrahydro-pyrano[3,4-b]indoles 6 were synthesized from 2-(2-trimethylsilanyl-1H-indol-3-yl)-ethanols 5 and various ketones or aldehydes through silicon-directed oxa-Pictet-Spengler cyclizations. An unusual reaction led to the dimeric products 7 when some of 5 was treated with acetone using BF(3) as the catalyst.
Zhang
Xuqing
X
Drug Discovery, Johnson & Johnson Pharmaceutical Research & Development, L.L C., Raritan, New Jersey 08869, USA. xzhang5@prdus.jnj.com
Li
Xiaojie
X
Lanter
James C
JC
Sui
Zhihua
Z
D002384:Catalysis; D003500:Cyclization; D000431:Ethanol / Q000031:analogs & derivatives / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D012825:Silicon / Q000737:chemistry*; D014297:Trimethylsilyl Compounds / Q000737:chemistry*; D014753:Vinyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D000438:Alcohols
D000431:Ethanol; D007211:Indoles; D012825:Silicon; D014297:Trimethylsilyl Compounds; D014753:Vinyl Compounds; C005949:tryptophol; D000438:Alcohols