PIGMENTS OF FUNGI .38. SYNTHESIS OF AUSTROCORTICINIC ACID AND (S)-(-)AUSTROCORTICIN - ABSOLUTE STEREOCHEMISTRY OF NATURAL AUSTROCORTICIN

被引：17

作者：

COTTERILL, AS ^{[1
]}

GILL, M ^{[1
]}

GIMENEZ, A ^{[1
]}

MILANOVIC, NM ^{[1
]}

机构：

[1] UNIV MELBOURNE,SCH CHEM,PARKVILLE,VIC 3052,AUSTRALIA

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 22期

关键词：

D O I：

10.1039/p19940003269

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The absolute configuration of the fungal anthraquinone (+)-austrocorticin 1 is established as (R) by synthesis of its antipode 5 from (S)-(-)-but-3-yn-2-ol via a Diels-Alder reaction involving the highly functionalised, chiral butadiene 6. Similarly, austrocorticinic acid is made available from but-1-yne.

引用

页码：3269 / 3276

页数：8

共 18 条

[1] ALLENES .7. SYNTHESIS OF IODOALLENES AND IODOACETYLENES [J].

BAKER, CSL ;

LANDOR, PD ;

LANDOR, SR ;

PATEL, AN .

JOURNAL OF THE CHEMICAL SOCIETY, 1965, (AUG) :4348-&

[2] REACTIONS OF KETENE ACETALS .8. SIMPLE SYNTHESES OF METHYL ESTER ETHERS OF ANTHRAQUINONES ENDOCROCIN, PTILOMETRIC ACID, AND CLAVORUBIN [J].

BANVILLE, J ;

BRASSARD, P .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (18) :3018-3020

[3] ENAMINE CHEMISTRY .3. REACTION OF KETENE ACETALS, O,N-ACETALS, AND N,N-ACETALS WITH ACETYLENIC ESTERS [J].

BRANNOCK, KC ;

THWEATT, JG ;

BURPITT, RD .

JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (06) :1697-&

[4]

Buckingham J., 1996, DICT ORGANIC COMPOUN

[5] BORON-TRICHLORIDE AS A SELECTIVE DEMETHYLATING AGENT FOR HINDERED ETHERS - A SYNTHESIS OF THE PHYTOALEXINS ALPHA-PYRUFURAN AND BETA-PYRUFURAN, A SYNTHESIS OF TRI-O-METHYLLEPROLOMIN AND ITS DEMETHYLATION [J].

CARVALHO, CF ;

RUSSO, AV ;

SARGENT, MV .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1985, 38 (05) :777-792

[6] THE TROUBLE WITH SYNTHESIS [J].

CORNFORTH, JW .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1993, 46 (02) :157-170

[7] PIGMENTS OF FUNGI .32. SYNTHESIS OF (S)-(-)-AUSTROCORTICIN AND (S)-(+)-DERMOLACTONE - ABSOLUTE STEREOCHEMISTRY OF THE NATURAL-PRODUCTS [J].

COTTERILL, AS ;

GILL, M .

TETRAHEDRON LETTERS, 1993, 34 (19) :3155-3158

[8]

COTTERILL AS, 1994, AUST J CHEM, V47, P363

[9] ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].

DALE, JA ;

DULL, DL ;

MOSHER, HS .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&

[10]

ELIEL EL, 1962, STEREOCHEMISTRY CARB, P43

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