INTRAMOLECULAR ADDITIONS OF ALLYSILANES TO CONJUGATED DIENONES - A DIRECT STEREOSELECTIVE SYNTHESIS OF (+/-)-14-DEOXYISOAMIJIOL

被引：63

作者：

MAJETICH, G ^{[1
]}

SONG, JS ^{[1
]}

RINGOLD, C ^{[1
]}

NEMETH, GA ^{[1
]}

NEWTON, MG ^{[1
]}

机构：

[1] UNIV TOLEDO, DEPT CHEM, TOLEDO, OH 43606 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 12期

关键词：

D O I：

10.1021/jo00012a035

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A 16-step synthesis of (+/-)-14-deoxyisoamijiol is reported featuring an intramolecular addition of an allylsilane to a conjugated dienone to construct stereospecifically the dolastane skeleton.

引用

页码：3973 / 3988

页数：16

共 86 条

[31]

HAYASHI T, 1982, J AM CHEM SOC, V104, P4963, DOI 10.1021/ja00382a046

[32] OPTICALLY-ACTIVE ALLYLSILANES .1. PREPARATION BY PALLADIUM-CATALYZED ASYMMETRIC GRIGNARD CROSS-COUPLING AND ANTI STEREOCHEMISTRY IN ELECTROPHILIC SUBSTITUTION-REACTIONS [J].

HAYASHI, T ;

KONISHI, M ;

ITO, H ;

KUMADA, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (18) :4962-4963

[33]

HILL RK, 1984, ASYMMETRIC SYNTHESIS, V3, P554

[34]

HIRAGA K, 1967, CHEM PHARM BULL, V13, P1359

[35] LATENT ACETONYLATION OF ALPHA,BETA-ENONES WITH ALLYLTRIMETHYLSILANE OR 2-METHYL-2-PROPENYLTRIMETHYLSILANE - SYNTHESIS OF 1,5-DIKETONES AND ANNELATION TO FUSED CYCLOHEXENONES [J].

HOSOMI, A ;

KOBAYASHI, H ;

SAKURAI, H .

TETRAHEDRON LETTERS, 1980, 21 (10) :955-958

[36] PERHYDROAZULENES .3. CONFORMATIONS OF THE 4-OXOPERHYDROAZULENES [J].

HOUSE, HO ;

GAA, PC ;

VANDERVEER, D .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (10) :1661-1670

[37] ALLYLIC REARRANGEMENTS .41. THE REACTION OF THIONYL CHLORIDE WITH STEROID ALLYLIC ALCOHOLS [J].

IRELAND, RE ;

WRIGLEY, TI ;

YOUNG, WG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (17) :4604-4606

[38] MECHANISM OF SOLVOLYSIS OF 2-HALOGENOALKYLSILANES .I. STERIC ASPECTS [J].

JARVIE, AWP ;

HOLT, A ;

THOMPSON, J .

JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1969, (07) :852-&

[39]

KNOLKER HJ, 1990, SYNLETT, P429

[40] TRAJECTORY ANALYSIS .1. THEORETICAL-MODEL FOR NUCLEOPHILIC-ATTACK AT PI-SYSTEMS - THE STABILIZING AND DESTABILIZING ORBITAL TERMS [J].

LIOTTA, CL ;

BURGESS, EM ;

EBERHARDT, WH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (17) :4849-4852

← 1 2 3 4 5 6 7 8 9 →