TY - JOUR
T1 - Synthetic studies relevant to biosynthetic research on vitamin B12. Part 11. Modification of the east and west building blocks and study of different assembly methods for synthesis of isobacteriochlorins
AU - Battersby, Alan R.
AU - Block, Michael H.
AU - Leeper, Finian J.
AU - Zimmerman, Steven C.
PY - 1992/1/1
Y1 - 1992/1/1
N2 - The eastern and western building blocks required for the photochemical route to isobacteriochlorins have been synthesized by a C-C bond-forming step which leaves a cyano group on the bridge carbon, e.g. 5. Two methods have been developed to remove this cyano residue which use retro-Mannich reactions to eliminate either an aminomethyl group, resulting from reduction of the nitrile, or the corresponding sulfonamido group. Two effective ways to carry out the final steps of the isobacteriochlorin synthesis have also been developed.
AB - The eastern and western building blocks required for the photochemical route to isobacteriochlorins have been synthesized by a C-C bond-forming step which leaves a cyano group on the bridge carbon, e.g. 5. Two methods have been developed to remove this cyano residue which use retro-Mannich reactions to eliminate either an aminomethyl group, resulting from reduction of the nitrile, or the corresponding sulfonamido group. Two effective ways to carry out the final steps of the isobacteriochlorin synthesis have also been developed.
UR - http://www.scopus.com/inward/record.url?scp=0011108983&partnerID=8YFLogxK
U2 - 10.1039/P19920002189
DO - 10.1039/P19920002189
M3 - Article
AN - SCOPUS:0011108983
SN - 0300-922X
SP - 2189
EP - 2195
JO - Journal of the Chemical Society, Perkin Transactions 1
JF - Journal of the Chemical Society, Perkin Transactions 1
IS - 17
ER -