The chemistry and occurrence of taxane derivatives .28. Novel base-catalyzed rearrangement of the taxane skeleton

被引：9

作者：

Appendino, G ^{[1
]}

Fenoglio, I ^{[1
]}

VanderVelde, DG ^{[1
]}

机构：

[1] UNIV KANSAS,DEPT MED CHEM,LAWRENCE,KS 66045

来源：

JOURNAL OF NATURAL PRODUCTS | 1997年 / 60卷 / 05期

关键词：

D O I：

10.1021/np960667s

中图分类号：

Q94 [植物学];

学科分类号：

071001 ;

摘要：

Methanolysis of taxicin I esters afforded the 1,15-secotaxane 4, the result of a vinylogous retroaldol reaction followed by acetalization and a transannular hydride shift.

引用

页码：464 / 466

页数：3

共 15 条

[1] Synthesis of 7,9-nitrogen-substituted paclitaxel derivatives [J].

Appendino, G ;

Jakupovic, J ;

Varese, M ;

Belloro, E ;

Danieli, B ;

Bombardelli, E .

TETRAHEDRON LETTERS, 1996, 37 (43) :7837-7840

[2] TAXANES FROM TAXUS-BACCATA [J].

APPENDINO, G ;

GARIBOLDI, P ;

PISETTA, A ;

BOMBARDELLI, E ;

GABETTA, B .

PHYTOCHEMISTRY, 1992, 31 (12) :4253-4257

[3] THE PHYTOCHEMISTRY OF THE YEW TREE [J].

APPENDINO, G .

NATURAL PRODUCT REPORTS, 1995, 12 (04) :349-360

[4]

APPENDINO G, 1996, ALKALOIDS CHEM BIOL, V11, P237

[5] 1ST HEMISYNTHESIS OF A TAXANE COMPOUND WITH AN OXETANE GROUP IN POSITION 4 (20), 5 [J].

ETTOUATI, L ;

AHOND, A ;

POUPAT, C ;

POTIER, P .

TETRAHEDRON, 1991, 47 (47) :9823-9838

[6] Synthesis of azetidine-type taxanes [J].

Fenoglio, I ;

Nano, GM ;

VanderVelde, DG ;

Appendino, G .

TETRAHEDRON LETTERS, 1996, 37 (18) :3203-3206

[7]

JACOBI P, 1970, LIEBIGS ANN CHEM, V741, P13

[8] Identification of six taxine alkaloids from Taxus baccata needles [J].

Jenniskens, LHD ;

vanRozendaal, ELM ;

vanBeek, TA ;

Wiegerinck, PHG ;

Scheeren, HW .

JOURNAL OF NATURAL PRODUCTS, 1996, 59 (02) :117-123

[9] TAXUSPINE-D, A NEW TAXANE DITERPENE FROM TAXUS-CUSPIDATA WITH POTENT INHIBITORY ACTIVITY AGAINST CA2+-INDUCED DEPOLYMERIZATION OF MICROTUBULES [J].

KOBAYASHI, J ;

HOSOYAMA, H ;

SHIGEMORI, H ;

KOISO, Y ;

IWASAKI, S .

EXPERIENTIA, 1995, 51 (06) :592-595

[10]

MAGNUS P, 1995, TETRAHEDRON LETT, V36, P5331, DOI 10.1016/00404-0399(50)1084U-

← 1 2 →