TOTAL SYNTHESIS OF (-)-ACETOMYCIN

被引：17

作者：

TADANO, K

ISHIHARA, J

OGAWA, S

机构：

[1] Department of Applied Chemistry, Keio University, Hiyoshi, Kohoku-ku, Yokohama

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 18期

关键词：

D O I：

10.1016/0040-4039(90)80138-C

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantiospecific total synthesis of the rifled antibiotic (1) has been completed. The pentasubstituted tetrahydrofuran (3), efficiently obtained from D-glucose, was used as an enantiomerically pure starting material. © 1990.

引用

页码：2609 / 2612

页数：4

共 16 条

[1] STOFFWECHSELPRODUKTE VON ACTINOMYCETEN .39. ZUR BIOGENESE DES ACETOMYCINS [J].

BACHMANN, E ;

ZAHNER, H ;

PRELOG, V ;

GERLACH, H .

HELVETICA CHIMICA ACTA, 1963, 46 (02) :605-&

[2] THE STRUCTURE AND ABSOLUTE-CONFIGURATION OF ACETOMYCIN [J].

CANO, FH ;

FOCESFOCES, C ;

ELGUERO, J .

ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1988, 44 :919-921

[3] STOFFWECHSELPRODUKTE VON ACTINOMYCETEN .12. UBER DIE ISOLIERUNG UND CHARAKTERISIERUNG VON ACETOMYCIN [J].

ETTLINGER, L ;

GAUMANN, E ;

HUTTER, R ;

KELLERSCHIERLEIN, W ;

KRADOLFER, F ;

NEIPP, L ;

PRELOG, V ;

ZAHNER, H .

HELVETICA CHIMICA ACTA, 1958, 41 (01) :216-219

[4] STOFFWECHSELPRODUKTE VON ACTINOMYCETEN .13. UBER DIE KONSTITUTION VON ACETOMYCIN [J].

KELLERSCHIERLEIN, W ;

MIHAILOVIC, ML ;

PRELOG, V .

HELVETICA CHIMICA ACTA, 1958, 41 (01) :220-228

[5] BIOLOGICAL EFFECTS OF ACETOMYCIN .2. INACTIVATION BY ESTERASES INVITRO [J].

MAMBER, SW ;

MITULSKI, JD ;

BORONDY, PE ;

TUNAC, JB .

JOURNAL OF ANTIBIOTICS, 1987, 40 (01) :77-80

[6] BIOLOGICAL EFFECTS OF ACETOMYCIN .1. ACTIVITY AGAINST TUMOR-CELLS INVITRO AND INVIVO [J].

MAMBER, SW ;

MITULSKI, JD ;

HAMELEHLE, KL ;

FRENCH, JC ;

HOKANSON, GC ;

SHILLIS, JL ;

LEOPOLD, WR ;

VONHOFF, DD ;

TUNAC, JB .

JOURNAL OF ANTIBIOTICS, 1987, 40 (01) :73-76

[7] INTRODUCTION OF GEM-DIALKYL GROUP TO HEXOFURANOSE BY ORTHO ESTER CLAISEN REARRANGEMENT [J].

TADANO, K ;

IDOGAKI, Y ;

YAMADA, H ;

SUAMI, T .

CHEMISTRY LETTERS, 1985, (12) :1925-1928

[8] SYNTHESIS OF (3S,4S)-DIHYDRO-4-ETHYL-3-HYDROXY-4-METHYL-2(3H)-FURANONE, A PANTOLACTONE HOMOLOG ISOLATED FROM MARSHALLIA-TENUIFOLIA [J].

TADANO, K ;

KANAZAWA, S ;

OGAWA, S .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (16) :3868-3870

[9] CLAISEN REARRANGEMENT OF (Z)-3-DEOXY-3-C-[(HYDROXYMETHYL)METHYLENE]-1,2-5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-RIBO-HEXOFURANOSE WITH TRIETHYL ORTHOPROPIONATE [J].

TADANO, K ;

ISHIHARA, J ;

YAMADA, H ;

OGAWA, S .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (05) :1223-1227

[10] CLAISEN REARRANGEMENTS OF 5,6-DIDEOXY-1,2-ORTHO-ISOPROPYLIDENE-ALPHA-D-XYLO-HEPT-5-ENO-1,4-FURANOSE AND 5,6-DIDEOXY-1,2-ORTHO-ISOPROPYLIDENE-ALPHA-D-RIBO-HEPT-5-ENO-1,4-FURANOSE WITH TRIETHYL ORTHOACETATE [J].

TADANO, K ;

SHIMADA, K ;

MIYAKE, A ;

ISHIHARA, J ;

OGAWA, SC .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1989, 62 (12) :3978-3986

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