Stereoselective synthesis of functonatized dihydropyrans via a formal [4+2]-annulation of chiral crotylsilanes

被引:117
作者
Huang, HB
Panek, JS
机构
[1] Boston Univ, Metcalf Ctr Sci & Engn, Dept Chem, Boston, MA 02215 USA
[2] Boston Univ, Metcalf Ctr Sci & Engn, Ctr Streamlined Synth, Boston, MA 02215 USA
关键词
D O I
10.1021/ja002087u
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
引用
收藏
页码:9836 / 9837
页数:2
相关论文
共 35 条
[1]   Stereoselective synthesis of tetrahydropyrans via a formal [4+2]-cycloaddition of allylsilanes [J].
Angle, SR ;
El-Said, NA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (43) :10211-10212
[2]  
BERESIS RT, 1997, ORG SYNTH, V75, P78
[3]   AN ENOLATE CLAISEN ROUTE TO C-PYRANOSIDES - DEVELOPMENT AND APPLICATION TO AN IONOPHORE SYNTHON [J].
BURKE, SD ;
ARMISTEAD, DM ;
SCHOENEN, FJ ;
FEVIG, JM .
TETRAHEDRON, 1986, 42 (11) :2787-2801
[4]   POLYSUBSTITUTED DIHYDROPYRANS VIA THE ENOLATE CLAISEN REARRANGEMENT - A STEREOCONTROLLED ROUTE TO C-PYRANOSIDES [J].
BURKE, SD ;
ARMISTEAD, DM ;
SCHOENEN, FJ .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (22) :4320-4322
[5]   Tandem glycolate Claisen rearrangement/ring-closing metathesis: A stereochemically general synthesis of substituted dihydropyran-2-carboxylates [J].
Burke, SD ;
Ng, RA ;
Morrison, JA ;
Alberti, MJ .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (10) :3160-3161
[6]   PREPARATION OF ENANTIOENRICHED TETRAHYDROPYRIDINES BY IMINIUM ION-VINYLSILANE CYCLIZATIONS [J].
CASTRO, P ;
OVERMAN, LE ;
ZHANG, XM ;
MARIANO, PS .
TETRAHEDRON LETTERS, 1993, 34 (33) :5243-5246
[7]   Stereocontrolled synthesis of trisubstituted tetrahydropyrans [J].
Cloninger, MJ ;
Overman, LE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (05) :1092-1093
[8]   LEWIS ACID MEDIATED CONDENSATION OF ALKENOLS AND ALDEHYDES - A SELECTIVE SYNTHESIS OF TETRAHYDROPYRANS AND OXEPANES [J].
COPPI, L ;
RICCI, A ;
TADDEI, M .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (04) :911-913
[9]   A CONCISE AND STEREOSELECTIVE ROUTE TO THE PREDOMINANT STEREOCHEMICAL PATTERN OF THE TETRAHYDROPYRANOID ANTIBIOTICS - AN APPLICATION TO INDANOMYCIN [J].
DANISHEFSKY, SJ ;
DENINNO, S ;
LARTEY, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (07) :2082-2089
[10]   TOTAL SYNTHESIS OF ZINCOPHORIN [J].
DANISHEFSKY, SJ ;
SELNICK, HG ;
ZELLE, RE ;
DENINNO, MP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (13) :4368-4378