New skeletal rearrangements of C and D rings of a 13-oxobaccatin III derivative

被引:9
作者
Marder-Karsenti, R [1 ]
Dubois, J [1 ]
Chiaroni, A [1 ]
Riche, C [1 ]
Guénard, D [1 ]
Guéritte, F [1 ]
Potier, P [1 ]
机构
[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
关键词
D O I
10.1016/S0040-4020(98)00993-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
13-Oxobaccatin III (4) was oxidized to 7,13-dioxo D-secobaccatin III (5). This compound, when treated with base or cyanide ion, underwent rearrangements involving the rupture of the C-7,C-8 bond, the migration of the benzoyl and acetyl groups and intramolecular formation of new rings. Four new compounds were isolated and fully characterized. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:15833 / 15844
页数:12
相关论文
共 30 条
[21]   Syntheses and structure-activity relationships of novel nor-seco taxoids [J].
Ojima, I ;
Lin, SN ;
Chakravarty, S ;
Fenoglio, I ;
Park, YH ;
Sun, CM ;
Appendino, G ;
Pera, P ;
Veith, JM ;
Bernacki, RJ .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (05) :1637-1645
[22]   New rearranged products from the methylation of 13-oxobaccatin III [J].
Pinciroli, V ;
Ceccarelli, W ;
FusarBassini, D ;
Menichincheri, M ;
Mongelli, N ;
Vanotti, E .
TETRAHEDRON LETTERS, 1996, 37 (52) :9365-9368
[23]   PROMOTION OF MICROTUBULE ASSEMBLY INVITRO BY TAXOL [J].
SCHIFF, PB ;
FANT, J ;
HORWITZ, SB .
NATURE, 1979, 277 (5698) :665-667
[24]  
SHELDRICK GM, 1993, SHELXL93 PROGRAM REF
[25]  
SHELDRICK GM, 1986, SHELXS86 PROGRAM SOL
[26]  
Suffness M., 1995, TAXOL SCI APPL
[27]   PLANT ANTITUMOR AGENTS .6. ISOLATION AND STRUCTURE OF TAXOL, A NOVEL ANTILEUKEMIC AND ANTITUMOR AGENT FROM TAXUS-BREVIFOLIA [J].
WANI, MC ;
TAYLOR, HL ;
WALL, ME ;
COGGON, P ;
MCPHAIL, AT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (09) :2325-&
[28]   Synthesis of novel taxol analogs and evaluation of their biological activities [J].
Wender, PA ;
Lee, DS ;
Lal, TK ;
Horwitz, SB ;
Rao, S .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (14) :1941-1944
[29]   Skeletal rearrangement of A and B ring of 13-oxobaccatin III derivative [J].
Yu, CZ ;
Liu, ZY .
TETRAHEDRON LETTERS, 1997, 38 (23) :4133-4136
[30]   Acid catalyzed rearrangement and acyl migration studies on 9-dihydro-13-acetylbaccatin-III, a major taxane from Taxus canadensis [J].
Zamir, LO ;
Balachandran, S ;
Zheng, YF ;
Nedea, ME ;
Caron, G ;
Nikolakakis, A ;
Vishwakarma, RA ;
Sauriol, F ;
Mamer, O .
TETRAHEDRON, 1997, 53 (47) :15991-16008