FORMAL TOTAL SYNTHESIS OF (-)-DENDROBINE USING ZIRCONIUM PROMOTED CYCLIZATION - DETERMINATION OF THE ABSOLUTE-CONFIGURATION OF THE INTERMEDIARY TRICYCLIC KETONE

被引：18

作者：

MORI, M ^{[1
]}

SAITOH, F ^{[1
]}

UESAKA, N ^{[1
]}

SHIBASAKI, M ^{[1
]}

机构：

[1] UNIV TOKYO, FAC PHARMACEUT SCI, BUNKYO KU, TOKYO 113, JAPAN

来源：

CHEMISTRY LETTERS | 1993年 / 02期

关键词：

D O I：

10.1246/cl.1993.213

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The optical purity of (-)-dendrobine synthesized using zirconium promoted cyclization was improved and the absolute configuration of the intermediary tricyclic ketone was determined using the improved Mosher's method developed by Kusumi.

引用

页码：213 / 216

页数：4

共 17 条

[1] ZIRCONOCENE COMPLEXES OF IMINES - GENERAL-SYNTHESIS, STRUCTURE, REACTIVITY, AND INSITU GENERATION TO PREPARE GEOMETRICALLY PURE ALLYLIC AMINES [J].

BUCHWALD, SL ;

WATSON, BT ;

WANNAMAKER, MW ;

DEWAN, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (12) :4486-4494

[2] SYNTHESIS OF SUBSTITUTED PYRROLES VIA ZIRCONOCENE COMPLEXES OF IMINES [J].

BUCHWALD, SL ;

WANNAMAKER, MW ;

WATSON, BT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (02) :776-777

[3] PREPARATION OF ZIRCONIUM(II) COMPLEXES BY LIGAND-INDUCED REDUCTIVE ELIMINATION - BIS(ETA-5-CYCLOPENTADIENYL)BIS(PHOSPHINE)ZIRCONIUM(II)COMPLEXES AND THEIR REACTIONS [J].

GELL, KI ;

SCHWARTZ, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (10) :2687-2695

[4] STRUCTURES AND ABSOLUTE-CONFIGURATIONS OF NEW LOBANE DITERPENOIDS FROM THE OKINAWAN SOFT CORAL SINULARIA-FLEXIBILIS [J].

HAMADA, T ;

KUSUMI, T ;

ISHITSUKA, MO ;

KAKISAWA, H .

CHEMISTRY LETTERS, 1992, (01) :33-36

[5] BICYCLIZATION OF UNSATURATED HYDRAZONES MEDIATED BY ZIRCONOCENE COMPLEXES - A NEW ANNULATION STRATEGY BASED ON THE REDUCTIVE COCYCLIZATION OF AZOMETHINE LINKAGES WITH CARBON CARBON MULTIPLE BONDS [J].

JENSEN, M ;

LIVINGHOUSE, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (12) :4495-4496

[6] THE X-RAY AND NMR-STUDIES ON THE REGIOSELECTIVE AND STEREOSELECTIVE COURSES FOR INSERTION OF KETONES INTO THE S-CIS-DIENE AND S-TRANS-DIENE COMPLEXES OF ZIRCONIUM LEADING TO (Z)-1,2-OXAZIRCONACYCLOHEPT-4-ENES [J].

KAI, Y ;

KANEHISA, N ;

MIKI, K ;

KASAI, N ;

AKITA, M ;

YASUDA, H ;

NAKAMURA, A .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1983, 56 (12) :3735-3743

[7] ELUCIDATION OF THE ABSOLUTE-CONFIGURATIONS OF AMINO-ACIDS AND AMINES BY THE MODIFIED MOSHER METHOD [J].

KUSUMI, T ;

FUKUSHIMA, T ;

OHTANI, I ;

KAKISAWA, H .

TETRAHEDRON LETTERS, 1991, 32 (25) :2939-2942

[8] NUCLEOPHILIC AND ORGANOMETALLIC DISPLACEMENT-REACTIONS OF ALLYLIC COMPOUNDS - STEREOCHEMISTRY AND REGIOCHEMISTRY [J].

MAGID, RM .

TETRAHEDRON, 1980, 36 (13) :1901-1930

[9] THE USE OF DIETHYL AZODICARBOXYLATE AND TRIPHENYLPHOSPHINE IN SYNTHESIS AND TRANSFORMATION OF NATURAL-PRODUCTS [J].

MITSUNOBU, O .

SYNTHESIS-STUTTGART, 1981, (01) :1-28

[10] NOVEL SYNTHESIS OF NITROGEN-HETEROCYCLES USING ZIRCONIUM-PROMOTED REDUCTIVE COUPLING - FORMAL TOTAL SYNTHESIS OF DENDROBINE [J].

MORI, M ;

UESAKA, N ;

SHIBASAKI, M .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (13) :3519-3521

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