Total synthesis of natural (-)-combretastatin D-1.

被引:20
作者
Couladouros, EA
Soufli, IC
机构
[1] Department of Chemistry, Agricultural University of Athens, Athens, 118.55
关键词
D O I
10.1016/0040-4039(95)01987-S
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Combrestastatin D-1, (2), was synthesized via a 12 step sequence. Sharpless asymmetric dihydroxylation was used in order to introduce the appropriate asymmetry. Regiospecific cyclodehydration of the diol 3 gave the title compound in 96% ee.
引用
收藏
页码:9369 / 9372
页数:4
相关论文
共 13 条
[1]   TOTAL SYNTHESIS OF COMBRETASTATIN D-2 - INTRAMOLECULAR ULLMANN MACROCYCLIZATION REACTION [J].
BOGER, DL ;
SAKYA, SM ;
YOHANNES, D .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (13) :4204-4207
[2]  
BOIGEGRAIN R, 1976, TETRAHEDRON LETT, P1283
[3]   SYNTHESIS OF COMBRETASTATIN D-2 - AN EFFICIENT ROUTE TO CAFFRANE MACROLACTONES [J].
COULADOUROS, EA ;
SOUFLI, IC .
TETRAHEDRON LETTERS, 1994, 35 (25) :4409-4412
[4]   SYNTHESIS OF COMBRETASTATIN D-2+ [J].
DESHPANDE, VH ;
GOKHALE, NJ .
TETRAHEDRON LETTERS, 1992, 33 (29) :4213-4216
[5]   1ST SYNTHESIS OF A STRAINED 14-MEMBERED BIARYL ETHER LACTONE BY MACROLACTONIZATION [J].
JUSTUS, K ;
STEGLICH, W .
TETRAHEDRON LETTERS, 1991, 32 (41) :5781-5784
[6]   HIGH-FIELD FT NMR APPLICATION OF MOSHER METHOD - THE ABSOLUTE-CONFIGURATIONS OF MARINE TERPENOIDS [J].
OHTANI, I ;
KUSUMI, T ;
KASHMAN, Y ;
KAKISAWA, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (11) :4092-4096
[7]   ANTINEOPLASTIC AGENTS .160. ISOLATION AND STRUCTURE OF COMBRETASTATIN-D-1 - A CELL-GROWTH INHIBITORY MACROCYCLIC LACTONE FROM COMBRETUM-CAFFRUM [J].
PETTIT, GR ;
SINGH, SB ;
NIVEN, ML .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (25) :8539-8540
[8]   REGIOSELECTIVE CYCLODEHYDRATION OF CHIRAL DIOLS WITH DIETHOXYTRIPHENYLPHOSPHORANE, TRIPHENYLPHOSPHINE-TETRACHLOROMETHANE-POTASSIUM CARBONATE, AND TRIPHENYLPHOSPHINE-DIETHYL AZODICARBOXYLATE REAGENTS - A COMPARATIVE-STUDY [J].
ROBINSON, PL ;
BARRY, CN ;
BASS, SW ;
JARVIS, SE ;
EVANS, SA .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (26) :5396-5398
[9]   SYNTHESIS OF (+/-)-COMBRETASTATIN D-1 AND COMBRETASTATIN D-2 [J].
RYCHNOVSKY, SD ;
HWANG, K .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (18) :5414-5418
[10]   SYNTHESIS AND REVISED CONFIGURATION OF (+)-COMBRETASTATIN D-1 [J].
RYCHNOVSKY, SD ;
HWANG, KS .
TETRAHEDRON LETTERS, 1994, 35 (48) :8927-8930