Synthetic studies toward the bryostatins: A substrate-controlled approach to the a-ring

被引:32
作者
Keck, Gary E. [1 ]
Welch, Dennie S. [1 ]
Vivian, Paige K. [1 ]
机构
[1] Univ Utah, Dept Chem, Salt Lake City, UT 84112 USA
关键词
D O I
10.1021/ol061173h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of a C-1 - C-13 A-ring subunit of bryostatin 1 is detailed. The key features of the approach include the convergent fragment assembly with a highly stereoselective construction of the C-7-C-8 bond indicated above.
引用
收藏
页码:3667 / 3670
页数:4
相关论文
共 37 条
[21]   CATALYTIC ASYMMETRIC ALLYLATION OF ALDEHYDES [J].
KECK, GE ;
TARBET, KH ;
GERACI, LS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (18) :8467-8468
[22]   DRAMATIC EFFECTS OF OXYGEN SUBSTITUENTS ON 1,3-ASYMMETRIC INDUCTION IN ADDITIONS OF ALLYLTRIPHENYLSTANNANE TO BETA-ALKOXY ALDEHYDES - A CHEMICAL AND SPECTROSCOPIC INVESTIGATION [J].
KECK, GE ;
CASTELLINO, S ;
WILEY, MR .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (26) :5478-5480
[23]   Chemistry and clinical biology of the bryostatins [J].
Mutter, R ;
Wills, M .
BIOORGANIC & MEDICINAL CHEMISTRY, 2000, 8 (08) :1841-1860
[24]   THE CERIUM MEDIATED CONVERSION OF ESTERS TO ALLYLSILANES [J].
NARAYANAN, BA ;
BUNNELLE, WH .
TETRAHEDRON LETTERS, 1987, 28 (50) :6261-6264
[25]  
Ohmori K, 2000, ANGEW CHEM INT EDIT, V39, P2290
[26]   ANTI-NEOPLASTIC AGENTS .86. ISOLATION AND STRUCTURE OF BRYOSTATIN-1 [J].
PETTIT, GR ;
HERALD, CL ;
DOUBEK, DL ;
HERALD, DL ;
ARNOLD, E ;
CLARDY, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (24) :6846-6848
[27]   A facile synthesis of chiral ω-allyl- and ω-n-propyllactones via asymmetric allylboration of formyl esters with B-allyldiisopinocampheylborane [J].
Ramachandran, PV ;
Krzeminski, MP ;
Reddy, MVR ;
Brown, HC .
TETRAHEDRON-ASYMMETRY, 1999, 10 (01) :11-15
[28]   STRUCTURAL, MECHANISTIC, AND THEORETICAL ASPECTS OF CHELATION-CONTROLLED CARBONYL ADDITION-REACTIONS [J].
REETZ, MT .
ACCOUNTS OF CHEMICAL RESEARCH, 1993, 26 (09) :462-468
[29]   Configurational assignment of polyene macrolide antibiotics using the [13C]acetonide analysis [J].
Rychnovsky, SD ;
Rogers, BN ;
Richardson, TI .
ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (01) :9-17
[30]   REDUCTIONS OF CONJUGATED CARBONYL-COMPOUNDS WITH COPPER HYDRIDE - PREPARATIVE AND MECHANISTIC ASPECTS [J].
SEMMELHACK, MF ;
STAUFFER, RD ;
YAMASHITA, A .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (19) :3180-3188