TY - JOUR
T1 - Total Synthesis of balanol, Part 2.
T2 - Completion of the Synthesis and Investigation of the Structure and Reactivity of Two Key heterocyclic Intermediates
AU - Tanner, David Ackland
AU - Kelly, Nicholas
AU - Tedenborg, Lars
AU - Almario, Antonio
AU - Pettersson, Ingrid
AU - Csoeregh, Ingeborg
AU - Hoegberg, Thomas
PY - 1997
Y1 - 1997
N2 - A convergent enantioselective total synthesis of the natural product (-)-balanol (1) is described. In addition to benzophenone fragment 8, key intermediates are chiral bicyclic aziridine 3 and the corresponding epoxide 4, both of which undergo highly regio- and stereoselective nucleophilic ring-opening reactions, allowing control of the two stereogenic centres of the target molecule. The structure and reactivity of 3 and 4 have been investigated in some detail. (C) 1997 Elsevier Science Ltd.
AB - A convergent enantioselective total synthesis of the natural product (-)-balanol (1) is described. In addition to benzophenone fragment 8, key intermediates are chiral bicyclic aziridine 3 and the corresponding epoxide 4, both of which undergo highly regio- and stereoselective nucleophilic ring-opening reactions, allowing control of the two stereogenic centres of the target molecule. The structure and reactivity of 3 and 4 have been investigated in some detail. (C) 1997 Elsevier Science Ltd.
U2 - 10.1016/S0040-4020(97)00167-1
DO - 10.1016/S0040-4020(97)00167-1
M3 - Journal article
SN - 0040-4020
VL - 53
SP - 4857
EP - 4868
JO - Tetrahedron
JF - Tetrahedron
IS - 13
ER -