REGIOCONTROL BY REMOTE SUBSTITUENTS - A DIRECT TOTAL SYNTHESIS OF RACEMIC HONGCONIN

被引：28

作者：

KRAUS, GA

LI, J

GORDON, M

JENSEN, JH

机构：

[1] US DOE,AMES LAB,AMES,IA 50011

[2] US DOE,DEPT CHEM,AMES,IA 50011

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 08期

关键词：

D O I：

10.1021/jo00087a044

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of hongconin (1) has been completed. Key steps include the metalation of a benzylic alcohol, the formation of a six-membered ring ether via a mercury-mediated cyclization, and the regioselective installation of the naphthalene ring by way of a Diels-Alder reaction.

引用

收藏

页码：2219 / 2222

页数：4

相关论文

共 18 条

[1] AN EFFICIENT SYNTHESIS OF AKLAVINONE AND RELATED 11-DEOXYANTHRACYCLINONES [J].

BAUMAN, JG ;

HAWLEY, RC ;

RAPOPORT, H .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (10) :1569-1573

[2] THE DEVELOPMENT AND USE OF QUANTUM-MECHANICAL MOLECULAR-MODELS .76. AM1 - A NEW GENERAL-PURPOSE QUANTUM-MECHANICAL MOLECULAR-MODEL [J].

DEWAR, MJS ;

ZOEBISCH, EG ;

HEALY, EF ;

STEWART, JJP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (13) :3902-3909

[3] A GENERAL AND REGIOSPECIFIC ROUTE TO TETRACYCLIC ALKENES IN THE 11-DEOXYANTHRACYCLINONE SERIES - APPLICATION TO THE TOTAL SYNTHESIS OF (+/-)-AURAMYCINONE [J].

GESSON, JP ;

JACQUESY, JC ;

RENOUX, B .

TETRAHEDRON, 1984, 40 (22) :4743-4750

[4]

Hainan-Renmin Hospital Guanxinbin-Keyan-Xiaozu, 1977, HAINAN WEISHENG, P43

[5] INFLUENCE OF POLARIZATION FUNCTIONS ON MOLECULAR-ORBITAL HYDROGENATION ENERGIES [J].

HARIHARA.PC ;

POPLE, JA .

THEORETICA CHIMICA ACTA, 1973, 28 (03) :213-222

[6]

KHAN SD, 1987, J AM CHEM SOC, V109, P663

[7]

KRAUS GA, 1993, SYNLETT, P525

[8] REGIOSELECTIVE DIELS-ALDER REACTIONS - A SYNTHESIS OF THE LEFT-HAND PORTION OF CC-1065 [J].

KRAUS, GA ;

YUE, S ;

SY, J .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (02) :283-284

[9] DIELS-ALDER REACTIONS OF QUINONE SULFOXIDES [J].

KRAUS, GA ;

WOO, SH .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (01) :114-116

[10] REGIOCONTROL BY REMOTE SUBSTITUENTS - AN ENANTIOSELECTIVE TOTAL SYNTHESIS OF FRENOLICIN-B VIA A HIGHLY REGIOSELECTIVE DIELS-ALDER REACTION [J].

KRAUS, GA ;

LI, J ;

GORDON, MS ;

JENSEN, JH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (13) :5859-5860