TY - JOUR
T1 - Taxane diterpenes 5
T2 - Synthesis of the A- and C-rings: An unusual rearrangement of an N-hydroxyimino lactone
AU - Magnus, P.
AU - Westwood, N.
AU - Spyvee, M.
AU - Frost, C.
AU - Linnane, P.
AU - Tavares, F.
AU - Lynch, V.
PY - 1999/5/21
Y1 - 1999/5/21
N2 - Ring A of taxol was synthesized from the bromodiene 5 and acryloyl chloride to give 6, which was resolved by separation of diastereomers 7. Allylic oxidation of 7 gave 8, which on deprotection, esterification and reduction gave 11. Heating 11 followed by reduction and protection gave 13. The C-ring component was made using asymmetric Birch reduction methodology combined with standard functional group manipulations to give 28. Combining 13 and 28 gave 29, which was converted into 33. Thermolysis of 33 did not generate a nitrile oxide but rather ionized to an oxydienyl cation, eventually leading to 34.
AB - Ring A of taxol was synthesized from the bromodiene 5 and acryloyl chloride to give 6, which was resolved by separation of diastereomers 7. Allylic oxidation of 7 gave 8, which on deprotection, esterification and reduction gave 11. Heating 11 followed by reduction and protection gave 13. The C-ring component was made using asymmetric Birch reduction methodology combined with standard functional group manipulations to give 28. Combining 13 and 28 gave 29, which was converted into 33. Thermolysis of 33 did not generate a nitrile oxide but rather ionized to an oxydienyl cation, eventually leading to 34.
UR - http://www.scopus.com/inward/record.url?scp=0033591178&partnerID=8YFLogxK
UR - http://dx.doi.org/10.1016/S0040-4020(99)00305-1
U2 - 10.1016/S0040-4020(99)00305-1
DO - 10.1016/S0040-4020(99)00305-1
M3 - Article
AN - SCOPUS:0033591178
SN - 0040-4020
VL - 55
SP - 6435
EP - 6452
JO - Tetrahedron
JF - Tetrahedron
IS - 21
ER -