Enantioselective reductive coupling of alkynes and α-keto aldehydes via rhodium-catalyzed hydrogenation:: An approach to bryostatin substructures

被引：38
作者：
Cho, CW [1 ]
Krische, MJ [1 ]
机构：
[1] Univ Texas, Dept Chem & Biochem, Austin, TX 78712 USA
来源：
ORGANIC LETTERS | 2006年 / 8卷 / 05期
关键词：
D O I：
10.1021/ol052976s
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Hydrogen-mediated reductive coupling of glyoxal 2 and 1,3-enyne 3 provides (x-hydroxy ketone 4 in 70% yield and 91% enantiomeric excess. Notably, the benzylic ether and diene side chain of 4 remain intact under the conditions of hydrogen-mediated coupling. In four steps, alpha-hydroxy ketone 4 is converted to pyrans 8 and 9, which embody key structural features of the bryostatin recognition domain.
引用
收藏
页码：891 / 894
页数：4
相关论文
共 48 条
[1]   Approaches to the stereoselective total synthesis of biologically active natural products [J].
Baron, A ;
Ball, M ;
Bradshaw, B ;
Donnelly, S ;
Germay, O ;
Oller, PC ;
Kumar, N ;
Martin, N ;
O'Brien, M ;
Omori, H ;
Moore, C ;
Thomas, EJ .
PURE AND APPLIED CHEMISTRY, 2005, 77 (01) :103-117
[2]   An approach to the synthesis of the C(17)-C(27) fragment of bryostatins [J].
Baxter, J ;
Mata, EG ;
Thomas, EJ .
TETRAHEDRON, 1998, 54 (47) :14359-14376
[3]   STRUCTURAL CHARACTERIZATION OF A TRANSIENT INTERMEDIATE IN RHODIUM-CATALYZED ASYMMETRIC HOMOGENEOUS HYDROGENATION [J].
BROWN, JM ;
CHALONER, PA .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (08) :344-346
[4]   IDENTIFICATION OF A FURTHER TRANSIENT SPECIES RELATING TO RHODIUM-COMPLEX CATALYZED ASYMMETRIC HYDROGENATION [J].
BROWN, JM ;
CHALONER, PA ;
MORRIS, GA .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (12) :664-666
[5]   The clinical development of the bryostatins [J].
Clamp, A ;
Jayson, GC .
ANTI-CANCER DRUGS, 2002, 13 (07) :673-683
[6]   BRYOSTATINS - THE ASYMMETRIC-SYNTHESIS OF C1-C9 AND C11-C16 FRAGMENTS [J].
DEBRABANDER, J ;
VANHESSCHE, K ;
VANDEWALLE, M .
TETRAHEDRON LETTERS, 1991, 32 (24) :2821-2824
[7]  
DEBRABANDER J, 1994, SYNLETT, P231
[8]   Bryostatin: A novel asymmetric synthesis of the C-27-C-34 fragment starting from (R)-carvone as chiral template [J].
DeBrabander, J ;
Kulkarni, BA ;
GarciaLopez, R ;
Vandewalle, M .
TETRAHEDRON-ASYMMETRY, 1997, 8 (11) :1721-1724
[9]   Total synthesis of bryostatin 2 [J].
Evans, DA ;
Carter, PH ;
Carreira, EM ;
Charette, AB ;
Prunet, JA ;
Lautens, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (33) :7540-7552
[10]  
Evans DA, 1998, ANGEW CHEM INT EDIT, V37, P2354, DOI 10.1002/(SICI)1521-3773(19980918)37:17<2354::AID-ANIE2354>3.0.CO
12345