Exploitation of cyclopropane ring-cleavage reactions for the rapid assembly of tetracyclic frameworks related to gibberellins

被引:23
作者
Banwell, Martin G. [1 ]
Phillis, Andrew T. [1 ]
Willis, Anthony C. [1 ]
机构
[1] Australian Natl Univ, Res Sch Chem, Inst Adv Studies, Canberra, ACT 0200, Australia
关键词
D O I
10.1021/ol062224d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The readily available hexahydrofluorene 5 has been elaborated over six steps, including three involving cyclopropane ring-cleavage reactions, into compound 12 which incorporates the carbocyclic framework associated with gibberellins.
引用
收藏
页码:5341 / 5344
页数:4
相关论文
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[1]   π-allyl cation cyclisations initiated by silver(I)-promoted electrocyclic ring opening of ring-fused gem-dibromocyclopropanes possessing tethered nucleophiles:: the influence of chiral auxiliaries on the diastereoselectivity of cyclisations involving meso-substrates [J].
Banwell, M ;
Edwards, A ;
Harvey, J ;
Hockless, D ;
Willis, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (14) :2175-2178
[2]  
Banwell M. G., UNPUB
[3]   Assembly of the 1-azaspiro[5.5] undecane framework associated with perhydrohistrionicotoxin via electrocyclic ring-opening of a ring-fused gem-dichlorocyclopropane and trapping of the resulting π-allyl cation by a tethered, nitrogen-centered nucleophile [J].
Banwell, Martin G. ;
Vogt, Florian ;
Wu, Angela W. .
AUSTRALIAN JOURNAL OF CHEMISTRY, 2006, 59 (07) :415-425
[4]   Pyrroles and gem-dihalocyclopropanes as building blocks for alkaloid synthesis [J].
Banwell, MG ;
Beck, DAS ;
Stanislawski, PC ;
Sydnes, MO ;
Taylor, RM .
CURRENT ORGANIC CHEMISTRY, 2005, 9 (15) :1589-1600
[5]   DEHYDROHALOGENATION OF THE BIS-DIHALOCARBENE ADDUCTS OF SOME METHOXYCYCLOHEXA-1,4-DIENES - REVISION OF PRODUCT STRUCTURES [J].
BANWELL, MG ;
GABLE, RW ;
HALTON, B ;
PHYLAND, JR .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1994, 47 (10) :1879-1884
[6]   Utilization of 1-aryl-2,2-dibromocyclopropanesin synthetic approaches to phenanthroquinolizidine and phenanthroindolizidine alkaloids [J].
Banwell, MG ;
Sydnes, MO .
AUSTRALIAN JOURNAL OF CHEMISTRY, 2004, 57 (06) :537-548
[7]   Total synthesis of (±)-rhazinal, an alkaloidal spindle toxin from Kopsia teoi [J].
Banwell, MG ;
Edwards, AJ ;
Jolliffe, KA ;
Smith, JA ;
Hamel, E ;
Verdier-Pinard, P .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (02) :296-305
[8]   Electrocyclic ring-opening/π-allyl cation cyclization reaction sequences involving gem-dihalocyclopropanes as substrates:: Application to syntheses of (±)-, (+)-, and (-)-γ-lycorane [J].
Banwell, MG ;
Harvey, JE ;
Hockless, DCR ;
Wu, AW .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (14) :4241-4250
[9]   Ring-fused gem-dibromocyclopropanes as precursors to enantiomerically pure D- and L-series 3-deoxy- and 2-amino-2,3-dideoxyaldohexose derivatives [J].
Banwell, MG ;
Ebenbeck, W ;
Edwards, AJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (02) :114-117
[10]   CYCLOHEXANNULATED [5.3.1]PROPELLANES AS PRECURSORS TO THE ABC RING-SYSTEM OF PACLITAXEL (TAXOL(TM)) [J].
BANWELL, MG ;
GABLE, RW ;
PETERS, SC ;
PHYLAND, JR .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (13) :1395-1397