NEW APPROACHES TO CORYNANTHE ALKALOIDS INVOLVING THE CONJUGATE ADDITION OF DIALKYL MALONATES TO UNSATURATED THIOLACTAMS - SYNTHESIS OF (+/-)-3-EPI-DIHYDROCORYNANTHEOL

被引：12

作者：

GOMEZPARDO, D

DESMAELE, D

DANGELO, J

机构：

[1] FAC PHARM CHATENAY MALABRY,CNRS,CHIM ORGAN LAB,5 RUE JB CLEMENT,F-92296 CHATENAY MALABRY,FRANCE

[2] CNRS,ECOLE SUPER PHYS & CHIM IND,UNITE CHIM ORGAN,F-75231 PARIS,FRANCE

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 44期

关键词：

MICHAEL ADDITION; UNSATURATED THIOLACTAMS; CORYNANTHE ALKALOIDS; (+/-)-3-EPI-DIHYDROCORYNANTHEOL;

D O I：

10.1016/S0040-4039(00)61004-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Addition of dimethyl malonate to thiolactam 8 led to a mixture of Michael adducts 9 and 10 (6:1, respectively). Compound 9 has been converted in 4 steps into (+/-)-3-epi-dihydrocorynantheol 16.

引用

页码：6633 / 6636

页数：4

共 14 条

[1] STEREOSELECTIVE TOTAL SYNTHESIS OF (+/-)-HIRSUTINE AND RELATED CORYNANTHE ALKALOIDS
BROWN, RT
JONES, MF
WINGFIELD, M
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (13) : 847 - 848
[2] STEREOSELECTIVE SYNTHESIS OF (+/-)DIHYDROANTIRHINE
FICINI, J
GUINGANT, A
DANGELO, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (05) : 1318 - 1319
[3] STEREOSELECTIVE ADDITIONS OF CHIRAL ALPHA-SULFINYL KETIMINE ANIONS TO ENE ESTERS - ASYMMETRIC SYNTHESES OF INDOLO[2,3-A]QUINOLIZIDINE AND YOHIMBAN ALKALOIDS
HUA, DH
BHARATHI, SN
PANANGADAN, JAK
TSUJIMOTO, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (25) : 6998 - 7007
[4] METHODS FOR INDOLE ALKALOID SYNTHESIS - A SPECIFIC PROCEDURE FOR INTRODUCING THE 6,7 DOUBLE-BOND INTO ASPIDOSPERMA-TYPE ALKALOIDS VIA THIOLACTAM DEHYDROGENATION
MAGNUS, P
PAPPALARDO, PA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (02) : 212 - 217
[5] AN ASYMMETRIC-SYNTHESIS AND ABSOLUTE-CONFIGURATION OF (S)-(-)-DEPLANCHEINE
MEYERS, AI
SOHDA, T
LOEWE, MF
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (16) : 3108 - 3112
[6] OHBA M, 1991, HETEROCYCLES, V32, P319
[7] TOTAL SYNTHESES OF (+)-GEISSOSCHIZINE, (+/-)-GEISSOSCHIZINE, AND (+/-)-(Z)-ISOSITSIRIKINE - STEREOCONTROLLED SYNTHESIS OF EXOCYCLIC DOUBLE-BONDS BY STEREOSPECIFIC IMINIUM ION VINYLSILANE CYCLIZATIONS
OVERMAN, LE
ROBICHAUD, AJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (01) : 300 - 308
[8] A CONVENIENT METHOD FOR THE SELECTIVE REDUCTION OF AMIDES TO AMINES
RAUCHER, S
KLEIN, P
[J]. TETRAHEDRON LETTERS, 1980, 21 (42) : 4061 - 4064
[9] SYNTHESIS OF AN OPTICALLY ACTIVE 13-BETA-METHYL 14-BETA-HYDROXY STEROID VIA BASE-CATALYZED REACTIONS
RUEL, R
DESLONGCHAMPS, P
[J]. TETRAHEDRON LETTERS, 1990, 31 (28) : 3961 - 3964
[10] RECENT PROGRESS IN THE CHEMISTRY OF INDOLE ALKALOIDS AND MOLD METABOLITES
SAXTON, JE
[J]. NATURAL PRODUCT REPORTS, 1991, 8 (03) : 251 - 307

← 1 2 →