TY - JOUR
T1 - Facile asymmetric construction of a functionalized dodecahydrobenz[a]indolo[3,2-h]quinolizine template
AU - Allin, Steven M.
AU - Duffy, Liam J.
AU - Towler, Joannah M.R.
AU - Bulman Page, Philip
AU - Elsegood, Mark R. J.
AU - Saha, Basu
PY - 2009/9/27
Y1 - 2009/9/27
N2 - We report a highly diastereoselective approach for the synthesis of a functionalized dodecahydrobenz[a]indolo[3,2-h]quinolizine ring system that is present as the heterocyclic core of the manadomanzamine alkaloids. We have achieved complete control over the relative and absolute stereochemistries at the three contiguous stereocentres at ring positions 1, 10 and 24 in only two linear synthetic steps. The introduction of useful functionality to the heterocyclic skeleton is significant as this may allow for future derivatization, and application of this route in an asymmetric synthesis of the manadomanzamine natural products.
AB - We report a highly diastereoselective approach for the synthesis of a functionalized dodecahydrobenz[a]indolo[3,2-h]quinolizine ring system that is present as the heterocyclic core of the manadomanzamine alkaloids. We have achieved complete control over the relative and absolute stereochemistries at the three contiguous stereocentres at ring positions 1, 10 and 24 in only two linear synthetic steps. The introduction of useful functionality to the heterocyclic skeleton is significant as this may allow for future derivatization, and application of this route in an asymmetric synthesis of the manadomanzamine natural products.
U2 - 10.1016/j.tet.2009.09.097
DO - 10.1016/j.tet.2009.09.097
M3 - Article
VL - 65
SP - 10230
EP - 10234
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 49
ER -