CONJUGQTE ADDITION OF HYDROGEN CYANIDE TO 5BETA-HYDROXY-10BETA-METHYL-1(9)-OCTAL-2-ONE . A REINVESTIGATION

被引：6

作者：

RAO, PN

BURDETT, JE

机构：

[1] Division of Biological Growth and Development, Department of Organic Chemistry, Southwest Foundation for Research and Education, San Antonio

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1969年 / 34卷 / 04期

关键词：

D O I：

10.1021/jo01256a068

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Conjugate addition of hydrogen cyanide to 5β-hydroxy-10β-methyl-1(9)-octal-2-one (2) gave a mixture of two ketonitriles (4a) and (4b). From unequivocal chemical studies and nmr spectral data the major product with mp 158-159° (4b) was assigned the trans configuration and the minor product with mp 189-190° (4a) was assigned the cis configuration. Earlier assignments of configuration of these compounds are revised. © 1969, American Chemical Society. All rights reserved.

引用

页码：1090 / &

共 21 条

[1] ADDITION OF HYDROGEN CYANIDE TO 9-METHYL-DELTA4-OCTALONE-3 AND 9BETA-METHYL-8BETA-HYDROXY-DELTA4-OCTALONE-3 [J].

BANERJEE, DK ;

ANGADI, VB .

TETRAHEDRON, 1965, 21 (02) :281-&

[2] SPIN-SPIN COUPLING BETWEEN HYDROGEN AND STEROID ANGULAR METHYL PROTONS [J].

BHACCA, NS ;

GURST, JE ;

WILLIAMS, DH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (02) :302-&

[3]

BUDZIKIEWICZ H, 1964, STRUCTURE ELUCIDATIO, V1, P17

[4]

BURDETT JE, 1968, THESIS STMARYS U TEX

[5]

HAUNGMINLON, 1946, J AM CHEM SOC, V68, P2487

[6] SYNTHETICAL STUDIES OF TERPENOIDS .8. SYNTHESIS OF (+)-10-METHYLTRICYCLO[7,2,1,01,6]DODECAN-11-ONE WITH NATURAL CONFIGURATION OF RINGS [J].

KUNDU, NG ;

DUTTA, PC .

JOURNAL OF THE CHEMICAL SOCIETY, 1962, (FEB) :533-&

[7] CONJUGATE ADDITION OF METHYLMAGNESIUM IODIDE TO 10-METHYL-1(9)-OCTAL-2-ONE . AN APPROACH TO VALERANONE CARBON FRAMEWORK [J].

MARSHALL, JA ;

FANTA, WI ;

ROEBKE, H .

JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (04) :1016-&

[8] LONG-RANGE SPIN-SPIN COUPLINGS IN NUCLEAR MAGNETIC RESONANCE SPECTRA OF BICYCLO[2.1.1]HEXANES [J].

MEINWALD, J ;

LEWIS, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (12) :2769-&

[9]

MEYER WL, 1962, J ORG CHEM, V27, P2011

[10] TOTALSYNTHETISCHE UNTERSUCHUNGEN AN STEROIDEN .9. EINFUHRUNG DER C-SUBSTITUENTEN IN DIE ANGULARE STELLUNG DER KONDENSIERTEN RINGSYSTEME .4. DARSTELLUNG VON RAC D-HOMO-18-OXO-ANDROSTAN-3BETA-OL-17-ON [J].

NAGATA, W .

TETRAHEDRON, 1961, 13 (04) :287-&

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