Synthetic studies on the DEF-rings of FR182877 and hexacyclinic acid

被引:25
作者
Clarke, PA
Grist, M
Ebden, M
Wilson, C
Blake, AJ
机构
[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England
[2] AstraZeneca Charnwood, Med Chem, Loughborough LE11 5RH, Leics, England
基金
英国工程与自然科学研究理事会;
关键词
transannular; lodocyclisation; natural products; medium sized rings;
D O I
10.1016/j.tet.2004.10.095
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A synthesis of model DEF-rings of the polyketide anti tumor natural products FR182877 and hexacyclinic acid has been achieved. The key steps in the synthesis are an intramolecular Pd(0) catalyzed allylic substitution reaction, which was used to generate a 9-membered carbocycle, and a novel transannular iodocyclization reaction which furnished the DF-rings of both natural products. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:353 / 363
页数:11
相关论文
共 40 条
[1]   Ruthenium carbene complexes with imidazolin-2-ylidene ligands allow the formation of tetrasubstituted cycloalkenes by RCM [J].
Ackermann, L ;
Fürstner, A ;
Weskamp, T ;
Kohl, FJ ;
Herrmann, WA .
TETRAHEDRON LETTERS, 1999, 40 (26) :4787-4790
[2]   A one-step synthesis of tetrahydropyranopyranones from carbonyl compounds [J].
Armstrong, A ;
Goldberg, FW ;
Sandham, DA .
TETRAHEDRON LETTERS, 2001, 42 (27) :4585-4587
[3]   REACTIONS OF IODINE(I) ACETATE WITH ALKENES AND VICINAL DIOLS [J].
CAMBIE, RC ;
RUTLEDGE, PS ;
STEWART, GM ;
WOODGATE, PD ;
WOODGATE, SD .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1984, 37 (08) :1689-1698
[4]   A NOVEL CYCLOAROMATIZATION REACTION .3. REGIO-CONTROLLED SYNTHESIS OF SUBSTITUTED PHENOLS [J].
CHAN, TH ;
BROWNBRIDGE, P .
TETRAHEDRON, 1981, 37 :387-391
[5]   Synthesis of the carbocyclic core of the cornexistins by ring-closing metathesis [J].
Clark, JS ;
Marlin, F ;
Nay, B ;
Wilson, C .
ORGANIC LETTERS, 2003, 5 (01) :89-92
[6]   An iodocyclisation/elimination approach to a DEF-ring core of FR182877 [J].
Clarke, PA ;
Grist, M ;
Ebden, M .
TETRAHEDRON LETTERS, 2004, 45 (05) :927-929
[7]   Synthesis of a model DEF-ring core of hexacyclinic acid [J].
Clarke, PA ;
Grist, M ;
Ebden, M ;
Wilson, C .
CHEMICAL COMMUNICATIONS, 2003, (13) :1560-1561
[8]   Access to [6.4.0]carbocyclic systems by tandem metathesis of dienynes.: A step toward the synthesis of a preD3-D3 transition state analogue [J].
Codesido, EM ;
Castedo, L ;
Granja, JR .
ORGANIC LETTERS, 2001, 3 (10) :1483-1486
[9]   pi-Allyl-palladium complexes stabilized by tripodal oxygen ligands [(C5H5)Co{P(OMe)(2)O}(3)](-) .2. Elimination instead of C-C coupling in reaction with resonance-stabilized carbanions [J].
Domhover, B ;
Klaui, W .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1996, 522 (02) :207-212
[10]   A cycloaddition cascade approach to the total synthesis of (-)-FR182877 [J].
Evans, DA ;
Starr, JT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (44) :13531-13540