179939-63-0Relevant academic research and scientific papers
The cis-specific Pictet-Spengler reaction
Alberch, Laura,Bailey, Patrick D.,Clingan, Paul D.,Mills, Timothy J.,Price, Richard A.,Pritchard, Robin G.
, p. 1887 - 1890 (2004)
The Pictet-Spengler reaction of tryptophan allyl ester with aryl aldehydes generates cis-tetrahydro-β-carbolines with complete stereo-control and with complete retention of optical integrity, when the reaction is carried out under kinetically controlled c
Stereoselectivity and conformational control in the synthesis of ajmaline and epi-ajmaline alkaloids
Bailey, Patrick D.,Beard, Mark A.,Cresswell, Mark,Dang, Hoa P.T.,Pathak, Ravindra B.,Phillips, Theresa R.,Price, Richard A.
, p. 1726 - 1729 (2013/04/24)
Careful choice of the N-protecting group provides crucial conformational control, allowing ring-closure to the indole 3-position in the late stages of the synthesis of ajmaline alkaloids; the choice of protecting group and reducing agent can also provide access to either the natural or epi configuration at the indole 2-position.
Unexpected cis selectivity in the Pictet-Spengler reaction
Bailey, Patrick D.,Beard, Mark A.,Phillips, Theresa R.
experimental part, p. 3645 - 3647 (2009/09/30)
Whilst cis:trans selectivity of about 4:1 can be obtained from Pictet-Spengler reactions between tryptophan methyl esters and aldehydes using conditions of kinetic control, much higher cis selectivity (>95:5) can be obtained when both the tryptophan deriv
The total synthesis of (-)-suaveoline
Bailey, Patrick D.,Morgan, Keith M.
, p. 3578 - 3583 (2007/10/03)
A new synthesis of the indole alkaloid (-)-suaveoline from L-tryptophan is reported (overall yield ca. 14%). Key synthetic steps include a high yielding cis-specific Pictet-Spengler reaction, a one-pot Horner-Wadsworth-Emmons and alkylation procedure, a vinylogous Thorpe cyclisation and the direct formation of a 3,4,5-trisubstituted pyridine from a 1,5-dinitrile. The direct conversion of ajmaline to semi-synthetic suaveoline is also described. The Royal Society of Chemistry 2000.
A total asymmetric synthesis of (-)-suaveoline
Bailey, Patrick D.,Morgan, Keith M.
, p. 1479 - 1480 (2007/10/03)
A new total synthesis of (-)-suaveoline from L-tryptophan is reported (overall yield ca. 14%); key steps include a high yielding cis-specific Pictet-Spengler reaction, a one-pot Horner-Wadsworth-Emmons/alkylation procedure, a vinylogous Thorpe cyclization
