A formal total synthesis of securinine via an intramolecular [4+2] cycloaddition reaction

被引：21

作者：

Honda, T ^{[1
]}

Namiki, H ^{[1
]}

Kudoh, M ^{[1
]}

Nagase, H ^{[1
]}

Mizutani, H ^{[1
]}

机构：

[1] Hoshi Univ, Fac Pharmaceut Sci, Shinagawa Ku, Tokyo 1428501, Japan

来源：

HETEROCYCLES | 2003年 / 59卷 / 01期

关键词：

D O I：

10.3987/COM-02-S11

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An intramolecular Diels-Alder reaction of the enol ester derived from 2-acetylpyridine and sorbic anhydride gave the cycloaddition product, stereoselectively, which was further converted into the key intermediate for the synthesis of securinine.

引用

页码：169 / 187

页数：19

共 14 条

[1] HIGHLY STEREOSELECTIVE TOTAL SYNTHESES OF (+)-ALLOPUMILIOTOXIN-267A AND (+)-ALLOPUMILIOTOXIN-339A VIA INTRAMOLECULAR NICKEL(II) CHROMIUM(II)-MEDIATED CYCLIZATION [J].

AOYAGI, S ;

WANG, TC ;

KIBAYASHI, C .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (24) :11393-11409

[2] APPROACHES TO CYTOCHALASAN SYNTHESIS - MACROCYCLE FORMATION USING AN INTRA-MOLECULAR DIELS-ALDER REACTION [J].

BAILEY, SJ ;

THOMAS, EJ ;

TURNER, WB ;

JARVIS, JAJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (11) :474-475

[3] SECURININE ALKALOIDS - A NEW CLASS OF GABA RECEPTOR ANTAGONIST [J].

BEUTLER, JA ;

KARBON, EW ;

BRUBAKER, AN ;

MALIK, R ;

CURTIS, DR ;

ENNA, SJ .

BRAIN RESEARCH, 1985, 330 (01) :135-140

[4] A novel intramolecular Diels-Alder approach to securinega alkaloids: formal synthesis of securinine [J].

Honda, T ;

Namiki, H ;

Kudoh, M ;

Watanabe, N ;

Nagase, H ;

Mizutani, H .

TETRAHEDRON LETTERS, 2000, 41 (31) :5927-5930

[5] TOTAL SYNTHESIS OF SECURININE AND VIROSECURININE [J].

HORII, Z ;

HANAOKA, M ;

YAMAWAKI, Y ;

TAMURA, Y ;

SAITO, S ;

SHIGEMATSU, N ;

KOTERA, K ;

YOSHIKAWA, H ;

SATO, Y ;

NAKAI, H ;

SUGIMOTO, N .

TETRAHEDRON, 1967, 23 (03) :1165-+

[6]

IMADO S, 1965, CHEM PHARM BULL, V13, P643

[7]

MURAVIEVA VI, 1956, DOKL AKAD NAUK SSSR+, V110, P998

[8] STUDIES ON ALKALOIDS OF SECURINEGA VIROSA PAX. ET HOFFM .1. STRUCTURE OF VIROSECURININE [J].

NAKANO, T ;

YANG, TH ;

TERAO, S .

TETRAHEDRON, 1963, 19 (04) :609-&

[9] STUDIES ON ALKALOIDS OF SECURINEGA VIROSA PAX ET HOFFM .2. ABSOLUTE CONFIGURATION OF C-6 IN VIROSECURININE AND STEREOCHEMICAL INTERRELATIONSHIP OF VIROSECURININE, SECURININE, AND ALLOSECURININE [J].

NAKANO, T ;

YANG, TH ;

TERAO, S .

JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (10) :2619-&

[10] STRUCTURE OF SECURININE [J].

SAITO, S ;

YAMAWAKI, Y ;

KOTERA, K ;

IDE, A ;

SHIGEMATSU, N ;

HORII, Z ;

HANAOKA, M ;

SUGIMOTO, N ;

TAMURA, Y .

TETRAHEDRON, 1963, 19 (12) :2085-&

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