Diastereoselective and convergent synthesis of both 11'-epimers of (-)-(2R,3R,6S)-carnavaline

被引：9

作者：

Pahl, A ^{[1
]}

Oetting, J ^{[1
]}

Holzkamp, J ^{[1
]}

Meyer, HH ^{[1
]}

机构：

[1] UNIV HANNOVER,INST ORGAN CHEM,D-30167 HANNOVER,GERMANY

来源：

TETRAHEDRON | 1997年 / 53卷 / 21期

关键词：

D O I：

10.1016/S0040-4020(97)00428-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantio- and diastereoselective syntheses of both 11'-epimers of (-)-carnavaline 1 have been achieved. Since the configuration of the remote chiral centre in the C-12 side chain of naturally occurring (-)-carnavaline had been unknown and spectroscopic data were not conclusive, an assignment of the 11'S-epimer to the natural product by comparison of the melting points is discussed and complete spectroscopic data are given. (C) 1997 Elsevier Science Ltd.

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页码：7255 / 7266

页数：12

相关论文

共 13 条

[1] FREE-RADICAL MACROCYCLIZATION VIA PROPIOLATE ESTERS [J].

BALDWIN, JE ;

ADLINGTON, RM ;

RAMCHARITAR, SH .

TETRAHEDRON, 1992, 48 (16) :3413-3428

[2] BIOACTIVE AND OTHER PIPERIDINE ALKALOIDS FROM CASSIA-LEPTOPHYLLA [J].

BOLZANI, VD ;

GUNATILAKA, AAL ;

KINGSTON, DGI .

TETRAHEDRON, 1995, 51 (21) :5929-5934

[3] PREPARATION OF OMEGA-BROMOALKAN-1-OLS FROM ALPHA, OMEGA-ALKANEDIOLS BY THE CONTINUOUS EXTRACTION METHOD [J].

CAMPS, F ;

CASAMOR, JM ;

COLL, J ;

GUERRERO, A ;

RIBA, M .

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1983, 15 (1-2) :63-67

[4] A NEW ROUTE TO OLEFIN COMPLEXES OF COPPER(I) COMPOUNDS [J].

COOK, BW ;

MILLER, RGJ ;

TODD, PF .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1969, 19 (02) :421-&

[5] HIGHLY ENANTIOSELECTIVE BORANE REDUCTION OF KETONES CATALYZED BY CHIRAL OXAZABOROLIDINES - MECHANISM AND SYNTHETIC IMPLICATIONS [J].

COREY, EJ ;

BAKSHI, RK ;

SHIBATA, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) :5551-5553

[6]

LYTHGOE D, 1967, TETRAHEDRON LETT, P1133

[7]

MEYER HH, 1997, TETRAHEDRON-ASYMMETR, V8, P477

[8] PYRROLE, PYRROLIDINE, PIPERIDINE, PYRIDINE, AND AZEPINE ALKALOIDS [J].

PINDER, AR .

NATURAL PRODUCT REPORTS, 1992, 9 (01) :17-23

[9] AZETIDINE, PYRROLE, PYRROLIDINE, PIPERIDINE, AND PYRIDINE ALKALOIDS [J].

PINDER, AR .

NATURAL PRODUCT REPORTS, 1992, 9 (05) :491-504

[10] PHOTOLACTONIZATION - A NOVEL SYNTHETIC ENTRY TO MACROLIDES [J].

QUINKERT, G ;

BILLHARDT, UM ;

JAKOB, H ;

FISCHER, G ;

GLENNEBERG, J ;

NAGLER, P ;

AUTZE, V ;

HEIM, N ;

WACKER, M ;

SCHWALBE, T ;

KURTH, Y ;

BATS, JW ;

DURNER, G ;

ZIMMERMANN, G ;

KESSLER, H .

HELVETICA CHIMICA ACTA, 1987, 70 (03) :771-861