RESOLUTION AND ABSOLUTE-CONFIGURATION OF A TRICYCLIC LACTONE - A POTENTIALLY USEFUL PRECURSOR OF HIGHLY FUNCTIONALIZED TERPENOIDS

被引：15

作者：

PREITE, MD ^{[1
]}

ZINCZUK, J ^{[1
]}

COLOMBO, MI ^{[1
]}

BACIGALUPPO, JA ^{[1
]}

GONZALEZSIERRA, M ^{[1
]}

RUVEDA, EA ^{[1
]}

机构：

[1] UNR,CONICET,FAC CIENCIAS BIOQUIM & FARMACEUT,INST QUIM ORGAN SINTESIS,CASILLA CORREO 991,RA-2000 ROSARIO,ARGENTINA

来源：

TETRAHEDRON-ASYMMETRY | 1993年 / 4卷 / 01期

关键词：

D O I：

10.1016/S0957-4166(00)86006-1

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The highly functionalized tricyclic lactone 1 was obtained in optically pure form by the sulfoximine-mediated resolution of the enone methyl acetal 3. The absolute configuration of (-)-3 and consequently of (+)-1, was determined by the transformation of (-)-3 into (-)-5, a known intermediate in the total synthesis of forskolin (2) and confirmed by application of the high field FT NMR Mosher method to alcohol 6.

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页码：17 / 20

页数：4

相关论文

共 13 条

[1] NOVEL SPONGE-DERIVED AMINO-ACIDS .11. THE ENTIRE ABSOLUTE STEREOCHEMISTRY OF THE BENGAMIDES [J].

ADAMCZESKI, M ;

QUINOA, E ;

CREWS, P .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (01) :240-242

[2] CONVENIENT AND SHORT ROUTE TO A KEY INTERMEDIATE IN THE SYNTHESIS OF FORSKOLIN [J].

BACIGALUPPO, JA ;

COLOMBO, MI ;

ZINCZUK, J ;

HUBER, SN ;

MISCHNE, MP ;

RUVEDA, EA .

SYNTHETIC COMMUNICATIONS, 1991, 21 (12-13) :1361-1367

[3] SYNTHETIC ROUTES TO FORSKOLIN [J].

COLOMBO, MI ;

ZINCZUK, J ;

RUVEDA, EA .

TETRAHEDRON, 1992, 48 (06) :963-1037

[4] SYNTHESIS OF THE ZIEGLER KEY INTERMEDIATE AND RELATED PRECURSORS FOR THE SYNTHESIS OF FORSKOLIN AND ERIGEROL [J].

COLOMBO, MI ;

ZINCZUK, J ;

BACIGALUPPO, JA ;

SOMOZA, C ;

RUVEDA, EA .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (21) :5631-5639

[5] A SHORT AND EFFICIENT ENANTIOSELECTIVE ROUTE TO A KEY INTERMEDIATE FOR THE TOTAL SYNTHESIS OF FORSKOLIN [J].

COREY, EJ ;

JARDINE, PD .

TETRAHEDRON LETTERS, 1989, 30 (52) :7297-7300

[6]

JOHNSON CR, 1985, ALDRICHIM ACTA, V18, P1001

[7]

KANEMATSU A, 1992, Patent No. 489486

[8]

NAGASHIMA S, 1990, TETRAHEDRON-ASYMMETR, V1, P743, DOI 10.1016/S0957-4166(00)82387-3

[9] HIGH-FIELD FT NMR APPLICATION OF MOSHER METHOD - THE ABSOLUTE-CONFIGURATIONS OF MARINE TERPENOIDS [J].

OHTANI, I ;

KUSUMI, T ;

KASHMAN, Y ;

KAKISAWA, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (11) :4092-4096

[10] INTRAMOLECULAR MICHAEL-ALDOL CONDENSATION APPROACH TO THE CONSTRUCTION OF ADVANCED INTERMEDIATES IN THE SYNTHESIS OF FORSKOLIN [J].

SOMOZA, C ;

DARIAS, J ;

RUVEDA, EA .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (07) :1539-1543