Rh-catalyzed triple allene approach to bicyclo[4.4.0]decene derivatives and its application for the stepwise synthesis of steroid-like tetracyclic skeletons

被引:36
作者
Lu, Ping [1 ]
Ma, Shengming [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organmet Chem, Shanghai 200032, Peoples R China
关键词
D O I
10.1021/ol702557s
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The construction of a new type of bicyclo[4.4.0]decene products with a conjugated exocyclic diene unit was developed using Rh-catalyzed cyclization of 1,5-bisallenes in the presence of monoallenes. The steroid-like tetracyclic products could be obtained by applying an alkylation-Diels-Alder process.
引用
收藏
页码:5319 / 5321
页数:3
相关论文
共 26 条
[1]   Open analogues of arcyriaflavin A.: Synthesis through Diels-Alder reaction between maleimides and 1-aryl-3-tert-butyldimethylsiloxy-1,3-butadienes [J].
Adeva, M ;
Sahagún, H ;
Caballero, E ;
de Clairac, RPL ;
Medarde, M ;
Tomé, F .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (11) :3387-3394
[2]   The behavior of 1,n-enynes in the presence of transition metals [J].
Aubert, C ;
Buisine, O ;
Malacria, M .
CHEMICAL REVIEWS, 2002, 102 (03) :813-834
[3]   Highly chemo-, regio-, and stereoselective [3+2]-cyclization of activated and deactivated allenes with alkenyl Fischer carbene complexes:: A straightforward access to alkylidenecyclopentanone derivatives [J].
Barluenga, Jose ;
Vicente, Ruben ;
Lopez, Luis A. ;
Tomas, Miguel .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) :7050-7054
[4]   Progress toward the total synthesis of (+)-aldosterone: Synthesis of the A-D rings [J].
Bear, BR ;
Parnes, JS ;
Shea, KJ .
ORGANIC LETTERS, 2003, 5 (10) :1613-1616
[5]   Rhodium(I)-catalyzed allenic carbocyclization reaction affording δ- and ε-lactams [J].
Brummond, Kay M. ;
Painter, Thomas O. ;
Probst, Donald A. ;
Mitasev, Branko .
ORGANIC LETTERS, 2007, 9 (02) :347-349
[6]   The allenic Alder-ene reaction: constitutional group selectivity and its application to the synthesis of ovalicin [J].
Brummond, Kay M. ;
McCabe, Jamie M. .
TETRAHEDRON, 2006, 62 (45) :10541-10554
[7]   Rhodium(I)-catalyzed ene-allene carbocyclization strategy for the formation of azepines and oxepines [J].
Brummond, KM ;
Chen, HF ;
Mitasev, B ;
Casarez, AD .
ORGANIC LETTERS, 2004, 6 (13) :2161-2163
[8]   Cobalt-catalyzed diastereoselective reductive [3+2] cycloaddition of allenes and enones [J].
Chang, Hong-Tai ;
Jayanth, Thiruvellore Thatai ;
Cheng, Chien-Hong .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (14) :4166-+
[9]   A TRIPLY CONVERGENT TOTAL SYNTHESIS OF 1(-)-PROSTAGLANDIN-E2 [J].
DONALDSON, RE ;
FUCHS, PL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (08) :2108-2110
[10]   Gold(I)- and gold(III)-catalyzed cycloisomerization of allenynes:: A remarkable halide effect [J].
Lemiere, Gilles ;
Gandon, Vincent ;
Agenet, Nicolas ;
Goddard, Jean-Philippe ;
de Kozak, Ariel ;
Aubert, Corinne ;
Fensterbank, Louis ;
Malacria, Max .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (45) :7596-7599