Synthesis of the C17-C27 fragment of bryostatin 3

被引:22
作者
Obitsu, T [1 ]
Ohmori, K [1 ]
Ogawa, Y [1 ]
Hosomi, H [1 ]
Ohba, S [1 ]
Nishiyama, S [1 ]
Yamamura, S [1 ]
机构
[1] Keio Univ, Fac Sci & Technol, Dept Chem, Yokohama, Kanagawa 2238522, Japan
关键词
biologically active compounds; macrolides; marine metabolites; polyketides;
D O I
10.1016/S0040-4039(98)01577-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The key synthetic intermediate corresponding to the C17 - C27 positions of bryostatin 3, has successfully been synthesized. The newly constructed stereogenic centers were unambiguously confirmed by X-ray crystallographic analysis. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:7349 / 7352
页数:4
相关论文
共 11 条
[1]   Towards the asymmetric synthesis of bryostatin 1 [J].
DeBrabander, J ;
Vandewalle, M .
PURE AND APPLIED CHEMISTRY, 1996, 68 (03) :715-718
[2]   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
[3]   Enantioselective synthesis of the C1-C9 segment of bryostatin by kinetic resolution of racemic alpha-keto esters [J].
Kalesse, M ;
Eh, M .
TETRAHEDRON LETTERS, 1996, 37 (11) :1767-1770
[4]   Asymmetric synthesis of the C(10)-C(16) segment of the bryostatins [J].
Lampe, TFJ ;
Hoffmann, HMR .
TETRAHEDRON LETTERS, 1996, 37 (43) :7695-7698
[5]   TOTAL SYNTHESIS OF BIOACTIVE MARINE MACROLIDES [J].
NORCROSS, RD ;
PATERSON, I .
CHEMICAL REVIEWS, 1995, 95 (06) :2041-2114
[6]   SYNTHETIC STUDIES ON BRYOSTATINS, ANTINEOPLASTIC METABOLITES - CONVERGENT SYNTHESIS OF THE C1-C16 FRAGMENT SHARED BY ALL OF THE BRYOSTATIN FAMILY [J].
OHMORI, K ;
SUZUKI, T ;
MIYAZAWA, K ;
NISHIYAMA, S ;
YAMAMURA, S .
TETRAHEDRON LETTERS, 1993, 34 (31) :4981-4984
[7]   Progress in the discovery of biosynthetic anticancer drugs [J].
Pettit, GR .
JOURNAL OF NATURAL PRODUCTS, 1996, 59 (08) :812-821
[8]   REVISED STRUCTURE OF BRYOSTATIN-3 AND ISOLATION OF THE BRYOSTATIN-3 26-KETONE FROM BUGULA-NERITINA [J].
SCHAUFELBERGER, DE ;
CHMURNY, GN ;
BEUTLER, JA ;
KOLECK, MP ;
ALVARADO, AB ;
SCHAUFELBERGER, BW ;
MUSCHIK, GM .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (08) :2895-2900
[9]   Synthesis of the first members of a new class of biologically active bryostatin analogues [J].
Wender, PA ;
De Brabander, J ;
Harran, PG ;
Jimenez, JM ;
Koehler, MFT ;
Lippa, B ;
Park, CM ;
Shiozaki, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (18) :4534-4535
[10]  
1994, ANN M CHEM SOC JAP