Regiocontrol in an intramolecular Schmidt reaction:: Total synthesis of (+)-aspidospermidine

被引:93
作者
Iyengar, R [1 ]
Schildknegt, K [1 ]
Aubé, J [1 ]
机构
[1] Univ Kansas, Dept Med Chem, Lawrence, KS 66045 USA
关键词
D O I
10.1021/ol005913c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A total synthesis of (+)-aspidospermidine (1) is described, featuring an intramolecular Schmidt reaction as the key step. The effects of stereochemistry and protecting group status on the regia and chemoselectivity of this reaction were examined.
引用
收藏
页码:1625 / 1627
页数:3
相关论文
共 36 条
[1]   INTRAMOLECULAR SCHMIDT REACTION OF ALKYL AZIDES [J].
AUBE, J ;
MILLIGAN, GL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (23) :8965-8966
[2]  
BAN Y, 1965, TETRAHEDRON LETT, P2261
[3]  
BAN Y, 1969, TETRAHEDRON LETT, P2523
[4]   NOVEL PHOTO-ISOMERIZATION OF 1-ACYLINDOLES TO 3-ACYLINDOLENINES - GENERAL ENTRY TO THE TOTAL SYNTHESIS OF STRYCHNOS AND ASPIDOSPERMA ALKALOIDS [J].
BAN, Y ;
YOSHIDA, K ;
GOTO, J ;
OISHI, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (23) :6990-6992
[5]   A novel route to (±)-aspidospermidine:: First application of "radical-polar crossover" reactions to total synthesis [J].
Callaghan, O ;
Lampard, C ;
Kennedy, AR ;
Murphy, JA .
TETRAHEDRON LETTERS, 1999, 40 (01) :161-164
[6]   A novel total synthesis of (±)-aspidospermidine [J].
Callaghan, O ;
Lampard, C ;
Kennedy, AR ;
Murphy, JA .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (08) :995-1001
[7]  
CAMERMAN A, 1965, TETRAHEDRON LETT, P637
[8]   THE ASYMMETRIC MICHAEL ADDITION-REACTIONS USING CHIRAL IMINES [J].
DANGELO, J ;
DESMAELE, D ;
DUMAS, F ;
GUINGANT, A .
TETRAHEDRON-ASYMMETRY, 1992, 3 (04) :459-505
[9]   STEREOCONTROLLED ELABORATION OF QUATERNARY CARBON CENTERS THROUGH THE ASYMMETRIC MICHAEL REACTION USING CHIRAL IMINES - ENANTIOSELECTIVE SYNTHESIS OF (+)-ASIDOSPERMIDINE [J].
DESMAELE, D ;
DANGELO, J .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (09) :2292-2303
[10]   D-ring substituted rhazinilam analogues:: Semisynthesis and evaluation of antitubulin activity [J].
Dupont, C ;
Guénard, D ;
Tchertanov, L ;
Thoret, S ;
Guéritte, F .
BIOORGANIC & MEDICINAL CHEMISTRY, 1999, 7 (12) :2961-2969