85925-68-4Relevant academic research and scientific papers
Vinyl Azides in Heterocyclic Synthesis. Part 9. Synthesis of the Isoquinolone Alkaloid Siamine by Intramolecular Aza-Wittig Reaction
Kennedy, Michael,Moody, Christopher J.,Rees, Charles W.,Vaquero, Juan J.
, p. 1395 - 1398 (2007/10/02)
The isoquinolone alkaloid siamine (1) has been synthesised from 3,5-dibenzyloxybenzoic acid (2) by a route which incorporates an intramolecular aza-Wittig reaction as the key step.The benzaldehyde (5), prepared from the benzoic acid (2) by the dihydro-oxa
General Method for the Synthesis of Phthalaldehydic Acids and Phthalides from o-Bromobenzaldehydes via Ortho-Lithiated Aminoalkoxides
Sinhababu, Achintya K.,Borchardt, Ronald T.
, p. 2356 - 2360 (2007/10/02)
A general method for the synthesis of phthalaldehydic acids and phthalides, many of which are key intermediates in natural product synthesis, has been developed. o-Bromobenzaldehydes 1a-f were first protected in situ as α-morpholinoalkoxides by reaction with lithium morpholide.Treatment of the α-morpholinoalkoxides 3a-f with n-butyllithium (to exchange bromine with lithium) followed by sequential treatment with solid CO2 and dilute acid afforded the phthalaldehydic acids 6a-f, respectively.Reduction of 6a-f with NaBH4 in EtOH furnished the phthalides 7a-f, respectively, in nearly quantitative yields.Efficient methods for the synthesis of the o-bromobenzaldehydes 1a-d, which were not readily available, are also described.
