DOUBLE DIOXANONE-TO-DIHYDROPYRAN REORGANIZATION - CONSTRUCTION OF A C(1)-C(13) ERYTHRONOLIDE TEMPLATE

被引:18
作者
BURKE, SD
LEE, KC
SANTAFIANOS, D
机构
[1] Department of Chemistry, University of Wisconsin-Madison, Madison
关键词
ERYTHRONOLIDE PRECURSOR; DOUBLE IRELAND-CLAISEN REARRANGEMENT;
D O I
10.1016/0040-4039(91)80599-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Convergent, stereoselective construction of the lactate-derived bis(dioxananone) 16 and two concurrent [3 3] sigmatropic transformations thereof result in the trienic bis(dihydropyran) 2, a potential precursor of the intact C(1)-C(13) erythronolide array.
引用
收藏
页码:3957 / 3960
页数:4
相关论文
共 45 条
[1]  
Boeckman R.K., 1988, TOTAL SYNTHESIS NATU, V7, P1
[2]   AN ALTERNATE ROUTE TO THE C(7)-C(13) SUBUNIT OF ERYTHRONOLIDE-B VIA A HYDROPYRAN TEMPLATE [J].
BURKE, SD ;
CHANDLER, AC ;
NAIR, MS ;
CAMPOPIANO, O .
TETRAHEDRON LETTERS, 1987, 28 (36) :4147-4148
[3]   THE ESTER ENOLATE CLAISEN REARRANGEMENT - SYNTHESIS OF A C(1)-C(6) ERYTHRONOLIDE FRAGMENT [J].
BURKE, SD ;
SCHOENEN, FJ ;
MURTIASHAW, CW .
TETRAHEDRON LETTERS, 1986, 27 (04) :449-452
[4]   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
[5]   THE DIOXANONE-TO-DIHYDROPYRAN CLAISEN REARRANGEMENT - SYNTHESIS OF C(7)-C(13) FRAGMENTS OF ERYTHRONOLIDE-A AND ERYTHRONOLIDE-B [J].
BURKE, SD ;
SCHOENEN, FJ ;
NAIR, MS .
TETRAHEDRON LETTERS, 1987, 28 (36) :4143-4146
[6]   STEREOCONTROLLED ONE-POT CONVERSIONS OF ALPHA-ALKOXY ESTERS TO SYN-1,2-DIOL AND ANTI-1,2-DIOL DERIVATIVES [J].
BURKE, SD ;
DEATON, DN ;
OLSEN, RJ ;
ARMISTEAD, DM ;
BLOUGH, BE .
TETRAHEDRON LETTERS, 1987, 28 (34) :3905-3906
[7]  
CAHIEZ G, 1976, SYNTHESIS-STUTTGART, P245
[8]   ENANTIOSELECTIVE TOTAL SYNTHESIS OF 9S-DIHYDROERYTHRONOLIDE-A SECO ACID [J].
CHAMBERLIN, AR ;
DEZUBE, M ;
REICH, SH ;
SALL, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (16) :6247-6256
[9]   MIXED CUPRATE REAGENTS OF TYPE R1R2CULI WHICH ALLOW SELECTIVE GROUP TRANSFER [J].
COREY, EJ ;
BEAMES, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (20) :7210-&
[10]   STEREOSELECTIVE SYNTHESIS OF "(+/-)-11-HYDROXY-TRANS-8-DODECENOIC ACID LACTONE, A NATURALLY OCCURRING MACROLIDE FROM CEPHALOSPORIUM-RECIFEI [J].
COREY, EJ ;
ULRICH, P ;
FITZPATRICK, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (01) :222-224