179939-66-3Relevant academic research and scientific papers
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.
Total synthesis of (-)-raumacline
Bailey, Patrick D.,Clingan, Paul D.,Mills, Timothy J.,Price, Richard A.,Pritchard, Robin G.
, p. 2800 - 2801 (2007/10/03)
The total synthesis of (-)-raumacline from L-tryptophan was achieved, featuring a cis-specific Pictet-Spengler reaction, a stereoselective Dieckmann cyclization, and an epimerization step that allowed complete stereocontrol of five chiral centres.
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
