Formal enantioselective synthesis of (+)-vincamine. The first enantioselective route to (+)-3,14-epivincamine and its enantiomer

被引：15

作者：

Alves, JCF ^{[1
]}

Simas, ABC ^{[1
]}

Costa, PRR ^{[1
]}

机构：

[1] Univ Fed Rio de Janeiro, Lab Sintese Assimetr LASA, CCS, BR-21941590 Rio De Janeiro, Brazil

来源：

TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 02期

关键词：

D O I：

10.1016/S0957-4166(98)00489-3

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A formal synthesis of (+)- vincamine (1) from (S)-(+)- 2-ethyl-2-(2-methoxycarbonylethyl) cyclopentanone (6a) is described. This intermediate had previously been obtained by our research group in 90% ee through d'Angelo's deracemizing alkylation of the chiral imine 7, easily prepared from (R)-(+)-alpha-methylbenzylamine and 2-ethyl cyclopentanone with methyl acrylate. A potencial advanced intermediate for the synthesis of (+)-4, an epimer of (+)-1 at positions C-3 and C-14, has also been prepared from 6a. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：297 / 306

页数：10

共 21 条

[1] Stereocontrolled elaboration of quaternary carbon centers involving the asymmetric Michael-type alkylation of chiral imines: An efficient enantioselective access to (+)-vincamine
Alves, JCF
Simas, ABC
Costa, PRR
dAngelo, J
[J]. TETRAHEDRON-ASYMMETRY, 1997, 8 (12) : 1963 - 1966
[2] SYNTHESIS OF COMPOUNDS RELATED TO VINCA ALKALOIDS - STEREOSELECTIVE SYNTHESIS OF (+/-) HOMOEBURNAMINE
BUZAS, A
RETOURNE, C
JACQUET, JP
LAVIELLE, G
[J]. TETRAHEDRON, 1978, 34 (19) : 3001 - 3004
[3] FORMAL SYNTHESIS OF (-)-VALLESAMIDINE A 2,2,3-TRIALKYLINDOLINE ALKALOID
COSTA, PRR
CASTRO, RN
FARIAS, FMC
ANTUNES, OAC
BERGTER, L
[J]. TETRAHEDRON-ASYMMETRY, 1993, 4 (07) : 1499 - 1500
[4] CZIBULA L, 1993, LIEBIGS ANN CHEM, P221
[5] THE ASYMMETRIC MICHAEL ADDITION-REACTIONS USING CHIRAL IMINES
DANGELO, J
DESMAELE, D
DUMAS, F
GUINGANT, A
[J]. TETRAHEDRON-ASYMMETRY, 1992, 3 (04) : 459 - 505
[6] Stereocontrolled elaboration of quaternary carbon centers through the asymmetric Michael-Type alkylation of chiral imines secondary enamines: Enantioselective synthesis of (+)-vincamine
Desmaele, D
Mekouar, K
dAngelo, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (12) : 3890 - 3901
[7] ALKYLMETAL ASYMMETRIC REDUCTION .18. STARTING MATERIALS IN THE PREPARATION OF NEW CHIRAL REDUCING AGENTS - SYNTHETIC APPROACH TO PRIMARY ALKYL-HALIDES DERIVED FROM (+)-CAMPHOR
FALORNI, M
LARDICCI, L
GIACOMELLI, G
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (26) : 5291 - 5294
[8] TOTAL SYNTHESIS OF THE INDOLE ALKALOIDS DL-EBURNAMONINE AND DL-VINCAMINE
HERRMANN, JL
CREGGE, RJ
RICHMAN, JE
KIECZYKOWSKI, GR
NORMANDIN, SN
QUESADA, ML
SEMMELHACK, CL
POSS, AJ
SCHLESSINGER, RH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (06) : 1540 - 1544
[9] KUEHNE ME, 1964, J AM CHEM SOC, V86, P2949
[10] CEMBRANOLIDE TOTAL SYNTHESIS - ANISOMELIC ACID
MARSHALL, JA
DEHOFF, BS
[J]. TETRAHEDRON, 1987, 43 (21) : 4849 - 4860

← 1 2 3 →