TY - JOUR
T1 - Stereoselectivity in the organoiron-mediated synthesis of (+/-)-mesembrine
AU - Roe, Caroline
AU - Sandoe, Elizabeth J.
AU - Stephenson, G. Richard
AU - Anson, Christopher E.
N1 - Roe, Caroline Sandoe, Elizabeth J. Stephenson, G. Richard Anson, Christopher E.
PY - 2008
Y1 - 2008
N2 - The preparation and structural characterisation of a 1-aryl-substituted electrophilic eta(5)-cyclohexadienyliron complex with the correct functionalisation as a 'C-12 building block' for the synthesis of (+/-)-mesembrine establishes the accessibility of a flattened conformation to allow nucleophile addition ipso to the arene. The chirality relay in quaternary centre formation by nucleophile addition has been confirmed, and the product has been converted into the Sceletium alkaloid mesembrine. (c) 2007 Elsevier Ltd. All rights reserved.
AB - The preparation and structural characterisation of a 1-aryl-substituted electrophilic eta(5)-cyclohexadienyliron complex with the correct functionalisation as a 'C-12 building block' for the synthesis of (+/-)-mesembrine establishes the accessibility of a flattened conformation to allow nucleophile addition ipso to the arene. The chirality relay in quaternary centre formation by nucleophile addition has been confirmed, and the product has been converted into the Sceletium alkaloid mesembrine. (c) 2007 Elsevier Ltd. All rights reserved.
U2 - 10.1016/j.tetlet.2007.11.137
DO - 10.1016/j.tetlet.2007.11.137
M3 - Article
VL - 49
SP - 650
EP - 653
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 4
ER -