FORMAL SYNTHESES OF HEPOXILIN B-3, TRIOXILIN B-3 AND SUBSTANCES EFFECTIVE AGAINST RICE BLAST DISEASE AND TOTAL SYNTHESES OF 11(R),12(S),13(S)-TRI-HYDROXYOCTADECA-9(Z),15(Z)-DIENOIC ACID

被引：14

作者：

WU, WL ^{[1
]}

WU, YL ^{[1
]}

机构：

[1] CHINESE ACAD SCI,SHANGHAI INST ORGAN CHEM,STATE KEY LAB BIOORGAN & NAT PROD CHEM,SHANGHAI 200032,PEOPLES R CHINA

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1993年 / 24期

关键词：

D O I：

10.1039/p19930003081

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereoselective conversion of readily available tri-O-isopropylidene-D-mannitol into the known synthetic intermediates for preparation of oxygenated fatty acids la, lb, 2a, 2b and 3a, 3b is described. Total synthesis of fatty acid 4a and preparation of the known intermediate for producing another substance effective against rice blast disease, 4b, from D-Xylose are also reported. These syntheses are based on a strategy of selective cleavage of isopropylidene acetals and lactol-formation-induced epimerization.

引用

页码：3081 / 3086

页数：6

共 23 条

[1] TOTAL SYNTHESIS OF 12-(S)-10-HYDROXY-TRANS-11,12-EPOXYEICOSA-5,9,14-(Z)-TRIENOIC ACIDS, METABOLITES OF ARACHIDONIC-ACID IN MAMMALIAN BLOOD-PLATELETS [J].

COREY, EJ ;

KANG, J ;

LAGUZZA, BC ;

JONES, RL .

TETRAHEDRON LETTERS, 1983, 24 (45) :4913-4916

[2]

DEMIN PM, 1990, BIOORG KHIM+, V16, P127

[3]

Hanessian S., 1983, TOTAL SYNTHESIS NATU

[4] IRON(III) AND COPPER(II) CATALYZED TRANSFORMATIONS OF FATTY-ACID HYDROPEROXIDES - EFFICIENT GENERATION OF PEROXY-RADICALS WITH COPPER(II) TRIFLUOROMETHANESULFONATE [J].

HAYNES, RK ;

VONWILLER, SC .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (16) :1102-1104

[5] ASYMMETRIC SYNTHESIS .2. STEROSPECIFIC SYNTHESIS OF BENZYLIC CENTRES - SOME 6-DEOXY-5-C-PHENYLHEXOSE DERIVATIVES [J].

INCH, TD ;

LEY, RV ;

RICH, P .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (13) :1683-&

[6] STRUCTURE AND SYNTHESIS OF 11,12,13-TRIHYDROXY-9Z,15Z-OCTADECADIENOIC ACIDS FROM RICE PLANT SUFFERING FROM RICE BLAST DISEASE [J].

KATO, T ;

YAMAGUCHI, Y ;

OHNUMA, S ;

UYEHARA, T ;

NAMAI, T ;

KODAMA, M ;

SHIOBARA, Y .

CHEMISTRY LETTERS, 1986, (04) :577-580

[7]

KATO T, 1986, J CHEM SOC CHEM COMM, P743

[8] SYNTHESIS OF SACCHARIDES AND RELATED POLYHYDROXYLATED NATURAL-PRODUCTS .3. EFFICIENT CONVERSION OF 2,3-ERYTHRO-ALDOSES TO 2,3-THREO-ALDOSES [J].

LEE, AWM ;

MARTIN, VS ;

MASAMUNE, S ;

SHARPLESS, KB ;

WALKER, FJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (12) :3515-3516

[9]

LUMIN W, 1988, TETRAHEDRON LETT, V29, P4239

[10] HEPOXILINS, POTENTIAL ENDOGENOUS MEDIATORS OF INSULIN RELEASE [J].

PACEASCIAK, CR ;

MARTIN, JM ;

COREY, EJ .

PROGRESS IN LIPID RESEARCH, 1986, 25 :625-628

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