Development of β-keto 1,3-dithianes as versatile intermediates for organic synthesis

被引:69
作者
Gaunt, MJ [1 ]
Sneddon, HF [1 ]
Hewitt, PR [1 ]
Orsini, P [1 ]
Hook, DF [1 ]
Ley, SV [1 ]
机构
[1] Univ Cambridge, Chem Lab, Cambridge CB2 1EW, England
关键词
D O I
10.1039/b208982c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
beta-Keto 1,3-dithianes can be generated by the double conjugate addition of dithiols to propargylic ketones, esters and aldehydes in excellent yields. As masked 1,3-dicarbonyl systems these substrates can be converted to a range of functionalised oxygen-containing heterocycles that can be used in natural product synthesis.
引用
收藏
页码:15 / 16
页数:2
相关论文
共 19 条
[1]   Synthesis of a 2,9-dioxabicyclo[3.3.1]nonane via double intramolecular hetero-Michael addition: Entry to the F-G ring system of the azaspiracids [J].
Aiguade, J ;
Hao, JL ;
Forsyth, CJ .
ORGANIC LETTERS, 2001, 3 (07) :979-982
[2]   SOME MOLECULAR-REARRANGEMENTS OF ORGANOSILICON COMPOUNDS [J].
BROOK, AG .
ACCOUNTS OF CHEMICAL RESEARCH, 1974, 7 (03) :77-84
[3]   Stereoselective synthesis of a family of alternating polyols from six-carbon epoxyalkynol modules [J].
Burova, SA ;
McDonald, FE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (28) :8188-8189
[4]   Application of complex aldol reactions to the total synthesis of phorboxazole B [J].
Evans, DA ;
Fitch, DM ;
Smith, TE ;
Cee, VJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (41) :10033-10046
[5]  
HATANAKA K, 1981, TETRAHEDRON LETT, P3243
[6]  
HAZELWOOD AJ, 2002, THESIS U CAMBRIDGE
[7]   Facile synthetic method for the preparation of dithioacetals by the double conjugate addition of acetylenes bearing electron-withdrawing groups with thiols [J].
Kuroda, H ;
Tomita, I ;
Endo, T .
SYNTHETIC COMMUNICATIONS, 1996, 26 (08) :1539-1543
[8]   TOTAL SYNTHESIS OF BIOACTIVE MARINE MACROLIDES [J].
NORCROSS, RD ;
PATERSON, I .
CHEMICAL REVIEWS, 1995, 95 (06) :2041-2114
[9]   A practical synthesis of (+)-discodermolide and analogues: Fragment union by complex aldol reactions [J].
Paterson, I ;
Florence, GJ ;
Gerlach, K ;
Scott, JP ;
Sereinig, N .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (39) :9535-9544
[10]   O-SILYLATED ENOLATES IN ORGANIC-SYNTHESIS - ALPHA-ALKYLATION OF CARBONYL-COMPOUNDS BY 1,3-DITHIENIUM FLUOROBORATE [J].
PATERSON, I ;
PRICE, LG .
TETRAHEDRON LETTERS, 1981, 22 (29) :2829-2832