CHIRAL SYNTHESIS OF POLYKETIDE-DERIVED NATURAL-PRODUCTS .22. A HIGHLY STEREOCONTROLLED TOTAL SYNTHESIS OF THE POLYETHER ANTIBIOTIC SALINOMYCIN - CRUCIAL ROLE OF THE 4-METHOXYBENZYL (MPM) PROTECTING GROUP FOR HYDROXY FUNCTIONS

被引：21

作者：

HORITA, K ^{[1
]}

OIKAWA, Y ^{[1
]}

NAGATO, S ^{[1
]}

YONEMITSU, O ^{[1
]}

机构：

[1] HOKKAIDO UNIV,FAC PHARMACEUT SCI,SAPPORO,HOKKAIDO 060,JAPAN

来源：

TETRAHEDRON LETTERS | 1988年 / 29卷 / 40期

关键词：

D O I：

10.1016/S0040-4039(00)80703-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

引用

页码：5143 / 5146

页数：4

共 25 条

[1]

COREY EJ, 1972, TETRAHEDRON LETT, P3769

[2] ON THE SELECTIVITY OF DEPROTECTION OF BENZYL, MPM (4-METHOXYBENZYL) AND DMPM (3,4-DIMETHOXYBENZYL) PROTECTING GROUPS FOR HYDROXY FUNCTIONS [J].

HORITA, K ;

YOSHIOKA, T ;

TANAKA, T ;

OIKAWA, Y ;

YONEMITSU, O .

TETRAHEDRON, 1986, 42 (11) :3021-3028

[3] STEREOSELECTIVE SYNTHESIS OF THE MIDDLE (C10-C17) AND RIGHT (C18-C30) SEGMENTS, AND THEIR COUPLING TO COMPLETE A FORMAL SYNTHESIS OF THE POLYETHER ANTIBIOTIC SALINOMYCIN [J].

HORITA, K ;

NAGATO, S ;

OIKAWA, Y ;

YONEMITSU, O .

TETRAHEDRON LETTERS, 1987, 28 (28) :3253-3256

[4]

KISHI Y, 1982, 28TH FRONT CHEM PLEN, P287

[5] SALINOMYCIN, A NEW POLYETHER ANTIBIOTIC [J].

MIYAZAKI, Y ;

SHIBUYA, M ;

SUGAWARA, H ;

KAWAGUCHI, O ;

HIROSE, C ;

NAGATSU, J ;

ESUMI, S .

JOURNAL OF ANTIBIOTICS, 1974, 27 (11) :814-821

[6] STEREOSELECTIVE SYNTHESIS OF PIKRONOLIDE, THE AGLYCON OF THE 14-MEMBERED RING MACROLIDE PIKROMYCIN, FROM D-GLUCOSE - CHIRAL SYNTHESIS OF POLYKETIDE-DERIVED NATURAL-PRODUCTS .10. ROLE OF MPM AND DMPM PROTECTION [J].

NAKAJIMA, N ;

HAMADA, T ;

TANAKA, T ;

OIKAWA, Y ;

YONEMITSU, O .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (15) :4645-4647

[7]

NAKAJIMA N, 1987, CHEM PHARM BULL, V35, P2228

[8]

OIKAWA Y, 1987, CHEM PHARM BULL, V35, P2196

[9] SELECTIVE HYDROGENOLYSIS OF THE BENZYL PROTECTING GROUP FOR HYDROXY FUNCTION WITH RANEY-NICKEL IN THE PRESENCE OF THE MPM (4-METHOXYBENZYL) AND DMPM (3,4-DIMETHOXYBENZYL) PROTECTING GROUPS [J].

OIKAWA, Y ;

TANAKA, T ;

HORITA, K ;

YONEMITSU, O .

TETRAHEDRON LETTERS, 1984, 25 (47) :5397-5400

[10] CHIRAL SYNTHESIS OF POLYKETIDE-DERIVED NATURAL-PRODUCTS .8. HIGHLY STEREOSELECTIVE SYNTHESIS OF METHYNOLIDE, THE AGLYCONE OF THE 12-MEMBERED RING MACROLIDE METHYMYCIN, FROM D-GLUCOSE [J].

OIKAWA, Y ;

TANAKA, T ;

YONEMITSU, O .

TETRAHEDRON LETTERS, 1986, 27 (31) :3647-3650

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