THE CHEMISTRY OF TAXANES - REACTION OF TAXOL AND BACCATIN DERIVATIVES WITH LEWIS-ACIDS IN APROTIC AND PROTIC MEDIA

被引：61

作者：

CHEN, SH

HUANG, S

WEI, JM

FARINA, V

机构：

[1] Bristol-Myers Squibb, Pharmaceutical Research Institute, Wallingford, CT 06492-7660

来源：

TETRAHEDRON | 1993年 / 49卷 / 14期

关键词：

D O I：

10.1016/S0040-4020(01)80381-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Several Lewis acids were shown to cleanly open the oxetane ring of taxol and baccatin derivatives. The reaction is shown to proceed via anchimeric assistance by the C-4 acetate group. Several minor products, including a novel derivative possessing a bridged C-ring, were also isolated. A mechanistic rationale is provided for all compounds formed. When taxol derivatives were treated with Lewis acids in methanol, ester cleavage reactions were observed. We provide conditions that are selective for C-10 acetate cleavage and for C-13 side-chain methanolysis.

引用

收藏

页码：2805 / 2828

页数：24

相关论文

共 14 条

[1] NUCLEAR OVERHAUSER EFFECT SPECTROSCOPY (NOESY) AND DIHEDRAL ANGLE MEASUREMENTS IN THE DETERMINATION OF THE CONFORMATION OF TAXOL IN SOLUTION [J].

BAKER, JK .

SPECTROSCOPY LETTERS, 1992, 25 (01) :31-48

[2] H-1 AND C-13 ASSIGNMENTS FROM SENSITIVITY-ENHANCED DETECTION OF HETERONUCLEAR MULTIPLE-BOND CONNECTIVITY BY 2D MULTIPLE QUANTUM NMR [J].

BAX, A ;

SUMMERS, MF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (08) :2093-2094

[3]

BELLON L, 1980, J ORG CHEM, V45, P1166, DOI 10.1021/jo01294a053

[4]

Deslongchamps P., 1983, STEREOELECTRONIC EFF

[5] NEW TAXANES FROM TAXUS-BREVIFOLIA .2. [J].

HUANG, CHO ;

KINGSTON, DGI ;

MAGRI, NF ;

SAMARANAYAKE, G ;

BOETTNER, FE .

JOURNAL OF NATURAL PRODUCTS, 1986, 49 (04) :665-669

[6] THE CHEMISTRY OF TAXOL [J].

KINGSTON, DGI .

PHARMACOLOGY & THERAPEUTICS, 1991, 52 (01) :1-34

[7] MODIFIED TAXOLS .3. PREPARATION AND ACYLATION OF BACCATIN-III [J].

MAGRI, NF ;

KINGSTON, DGI ;

JITRANGSRI, C ;

PICCARIELLO, T .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (16) :3239-3242

[8] THE ROLE OF NEIGHBORING GROUPS IN REPLACEMENT REACTIONS .24. THE ACETOXY GROUP - PREPARATION AND REACTIONS OF THE KETENE ACETAL OF CIS-1,2-CYCLOHEXANEDIOL (2-METHYLENE-CIS-4,5-TETRAMETHYLENEDIOXOLANE) [J].

ROBERTS, RM ;

CORSE, J ;

BOSCHAN, R ;

SEYMOUR, D ;

WINSTEIN, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (05) :1247-1254

[9] MODIFIED TAXOLS .5. REACTION OF TAXOL WITH ELECTROPHILIC REAGENTS AND PREPARATION OF A REARRANGED TAXOL DERIVATIVE WITH TUBULIN ASSEMBLY ACTIVITY [J].

SAMARANAYAKE, G ;

MAGRI, NF ;

JITRANGSRI, C ;

KINGSTON, DGI .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (17) :5114-5119

[10] TAXOL - A NEW AND EFFECTIVE ANTICANCER DRUG [J].

SLICHENMYER, WJ ;

VONHOFF, DD .

ANTI-CANCER DRUGS, 1991, 2 (06) :519-530