A NOVEL BIOGENETIC TYPE SYNTHESIS OF (+)-HYDANTOCIDIN

被引：41

作者：

MATSUMOTO, M ^{[1
]}

KIRIHARA, M ^{[1
]}

YOSHINO, T ^{[1
]}

KATOH, T ^{[1
]}

TERASHIMA, S ^{[1
]}

机构：

[1] SAGAMI CHEM RES CTR,SAGAMIHARA,KANAGAWA 229,JAPAN

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 39期

关键词：

BIOGENETIC TYPE SYNTHESIS; HYDANTOCIDIN; 5-EPI-HYDANTOCIDIN; HERBICIDE; BENZYLGLYCOCIDE FORMATION; INTRAMOLECULAR-N; O-SPIROKETAL FORMATION; D-PSICOSE; D-FRUCTOSE; UREA;

D O I：

10.1016/S0040-4039(00)73734-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The title synthesis was accomplished by featuring the proposed biosynthetic pathway. The synthesis commenced with the D-psicose derivative readily obtainable from D-fructose and employed intramolecular N, O-spiroketal formation of the open-chain N-acylurea derivative as a key step.

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页码：6289 / 6292

页数：4

相关论文

共 13 条

[1] SYNTHESIS OF 1-EPIHYDANTOCIDIN FROM D-RIBOSE [J].

FAIRBANKS, AJ ;

FORD, PS ;

WATKIN, DJ ;

FLEET, GWJ .

TETRAHEDRON LETTERS, 1993, 34 (20) :3327-3330

[2] STRUCTURAL ELUCIDATION AND SOLUTION CONFORMATION OF THE NOVEL HERBICIDE HYDANTOCIDIN [J].

HARUYAMA, H ;

TAKAYAMA, T ;

KINOSHITA, T ;

KONDO, M ;

NAKAJIMA, M ;

HANEISHI, T .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (07) :1637-1640

[3] SYNTHETIC STUDIES ON (+)-HYDANTOCIDIN (4) - SYNTHESIS OF STEREOISOMERS OF (+)-HYDANTOCIDIN [J].

MIO, S ;

UEDA, M ;

HAMURA, M ;

KITAGAWA, J ;

SUGAI, S .

TETRAHEDRON, 1991, 47 (12-13) :2145-2154

[4] SYNTHETIC STUDIES ON (+)-HYDANTOCIDIN (2) - ALDOL ADDITION APPROACHES TOWARD THE STEREOISOMERS OF (+)-HYDANTOCIDIN [J].

MIO, S ;

SHIRAISHI, M ;

SUGAI, S ;

HARUYAMA, H ;

SATO, S .

TETRAHEDRON, 1991, 47 (12-13) :2121-2132

[5] SYNTHETIC STUDIES ON (+)-HYDANTOCIDIN (3) - A NEW SYNTHETIC METHOD FOR CONSTRUCTION OF THE SPIRO-HYDANTOIN RING AT THE ANOMERIC POSITION OF D-RIBOFURANOSE [J].

MIO, S ;

KUMAGAWA, Y ;

SUGAI, S .

TETRAHEDRON, 1991, 47 (12-13) :2133-2144

[6] SYNTHETIC STUDIES ON (+)-HYDANTOCIDIN (1) - A TOTAL SYNTHESIS OF (+)-HYDANTOCIDIN, A NEW HERBICIDAL METABOLITE FROM MICROORGANISM [J].

MIO, S ;

ICHINOSE, R ;

GOTO, K ;

SUGAI, S ;

SATO, S .

TETRAHEDRON, 1991, 47 (12-13) :2111-2120

[7] SYNTHESIS AND HERBICIDAL ACTIVITY OF DEOXY DERIVATIVES OF (+)-HYDANTOCIDIN [J].

MIO, S ;

SANO, H ;

SHINDOU, M ;

HONMA, T ;

SUGAI, S .

AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1991, 55 (04) :1105-1109

[8]

MIO S, COMMUNICATION

[9]

MIO S, 1991, ANN REP SANKYO RES L, V43, P133

[10]

NAKAJIMA N, 1992, J ANTIBIOT, V44, P293