Organic and Biomolecular Chemistry p. 459 - 468 (2013)
Update date:2022-08-04
Topics:
Eyong, Kenneth O.
Puppala, Manohar
Kumar, Ponminor Senthil
Lamsh?ft, Marc
Folefoc, Gabriel N.
Spiteller, Michael
Baskaran, Sundarababu
The Hooker oxidation is one of the most intriguing transformations wherein lapachol (1) is readily converted to norlapachol (2) in very good yield. This one-pot reaction involves a very intricate mechanism in which the alkyl side chain of lapachol is shortened by one carbon unit. Previous studies have unequivocally established the involvement of an indane carboxylic acid derivative 3, as a key intermediate (Hooker intermediate), and its simultaneous conversion to norlapachol (2) via the oxidative cleavage of vicinol diol and subsequent intramolecular aldol reaction of the resulting keto acid. However, the formation of the key Hooker intermediate 3 from lapachol (1) remains ambiguous. The present study has thrown some light on the formation of the key intermediate 3 from lapachol (1) via benzilic acid rearrangement of the corresponding labile o-diquinone intermediate 8 derived from lapachol. The involvement of o-diquinone intermediate 8 in the Hooker oxidation has been further established by trapping of this labile intermediate as the corresponding phenazine derivative 9. The involvement of benzilic acid rearrangement as a key step in the Hooker oxidation is further shown with a variety of o-quinones prepared from lapachol (1). The Royal Society of Chemistry 2013.
View MoreNantong LiKai Chemical Co.,Ltd
Contact:+86-513-89068669
Address:Jincheng Science Park
NINGXIA DARONG CHEMICALS & METALLURGY CO.,LTD.
Contact:86-952-2179751
Address:Darong Road, Dawukou, Shizuishan, Ningxia 753001, China
Zibo Kunran Enterprises Co. LTD
website:http://www.kunranchem.com
Contact:0086 533 5200669
Address:No. 96 Jinjing Avenue, Zibo, Shandong, China
hangzhou verychem science and technology co.ltd
website:http://www.verypharm.com
Contact:+86-571-88162785; 88162786
Address:F1502, 753 Shenhua road, Hangzhou, China
Contact:0086-22-2822 1962 / 2822 1963
Address:B-808, No. 1, North-South Street, Hexi District,
Doi:10.1021/acs.orglett.0c02386
(2020)Doi:10.1021/jm00113a038
(1991)Doi:10.4314/bcse.v28i1.11
(2014)Doi:10.1016/j.bmcl.2012.11.054
(2013)Doi:10.1002/cmdc.201200334
(2012)Doi:10.1021/jo302421u
(2013)