共 33 条
Progress towards the total synthesis of tedanolide:: an efficient assembly of the C1-C11 subunit
被引:27
作者:

Loh, TP
论文数: 0 引用数: 0
h-index: 0
机构:
Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore

Feng, LC
论文数: 0 引用数: 0
h-index: 0
机构:
Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore
机构:
[1] Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore
关键词:
D O I:
10.1016/S0040-4039(01)01169-8
中图分类号:
O62 [有机化学];
学科分类号:
070303 ;
081704 ;
摘要:
The C-1-C-11 subunit of tedanolide was constructed using a boron-mediated syn aldol reaction as the key step to control the C-6 and C-7 stereocenters. Other features of this work include the asymmetric Sharpless dihydroxylation to incorporate the C-2, C-3 hydroxyl groups, selective protection of the hydroxyl group at C-2 as well as the usage of a tert-butyl ester to tolerate the attack of Grignard and enolate reagents. (C) 2001 Elsevier Science Ltd. All rights reserved.
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页码:6001 / 6005
页数:5
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共 33 条
- [1] ORIGINS OF STEREOSELECTIVITY IN CHIRAL BORON ENOLATE ALDOL REACTIONS - A COMPUTATIONAL STUDY USING TRANSITION-STATE MODELING[J]. TETRAHEDRON, 1991, 47 (20-21) : 3471 - 3484BERNARDI, A论文数: 0 引用数: 0 h-index: 0机构: UNIV MILAN,DIPARTIMENTO CHIM ORGAN & IND,VIA VENEZIAN 21,I-20133 MILAN,ITALYCAPELLI, AM论文数: 0 引用数: 0 h-index: 0机构: UNIV MILAN,DIPARTIMENTO CHIM ORGAN & IND,VIA VENEZIAN 21,I-20133 MILAN,ITALYCOMOTTI, A论文数: 0 引用数: 0 h-index: 0机构: UNIV MILAN,DIPARTIMENTO CHIM ORGAN & IND,VIA VENEZIAN 21,I-20133 MILAN,ITALYGENNARI, C论文数: 0 引用数: 0 h-index: 0机构: UNIV MILAN,DIPARTIMENTO CHIM ORGAN & IND,VIA VENEZIAN 21,I-20133 MILAN,ITALYGARDNER, M论文数: 0 引用数: 0 h-index: 0机构: UNIV MILAN,DIPARTIMENTO CHIM ORGAN & IND,VIA VENEZIAN 21,I-20133 MILAN,ITALYGOODMAN, JM论文数: 0 引用数: 0 h-index: 0机构: UNIV MILAN,DIPARTIMENTO CHIM ORGAN & IND,VIA VENEZIAN 21,I-20133 MILAN,ITALY论文数: 引用数: h-index:机构:
- [2] 3-HYDROXYLEUKOTRIENE B-4(3-OH-LTB(4)) - TOTAL SYNTHESIS AND STEREOCHEMICAL ASSIGNMENT[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (12) : 5050 - 5056BHATT, RK论文数: 0 引用数: 0 h-index: 0机构: UNIV TEXAS, SW MED CTR, DEPT MOLEC GENET, DALLAS, TX 75235 USACHAUHAN, K论文数: 0 引用数: 0 h-index: 0机构: UNIV TEXAS, SW MED CTR, DEPT MOLEC GENET, DALLAS, TX 75235 USAWHEELAN, P论文数: 0 引用数: 0 h-index: 0机构: UNIV TEXAS, SW MED CTR, DEPT MOLEC GENET, DALLAS, TX 75235 USAMURPHY, RC论文数: 0 引用数: 0 h-index: 0机构: UNIV TEXAS, SW MED CTR, DEPT MOLEC GENET, DALLAS, TX 75235 USAFALCK, JR论文数: 0 引用数: 0 h-index: 0机构: UNIV TEXAS, SW MED CTR, DEPT MOLEC GENET, DALLAS, TX 75235 USA
- [3] REACTION OF ORGANOBORANES WITH ETHYL BROMOACETATE UNDER INFLUENCE OF POTASSIUM T-BUTOXIDE . A CONVENIENT PROCEDURE FOR CONVERSION OF OLEFINS INTO ESTERS VIA HYDROBORATION[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (03) : 818 - &BROWN, HC论文数: 0 引用数: 0 h-index: 0ROGIC, MM论文数: 0 引用数: 0 h-index: 0RATHKE, MW论文数: 0 引用数: 0 h-index: 0KABALKA, GW论文数: 0 引用数: 0 h-index: 0
- [4] A MILD PROCEDURE FOR ETHERIFICATION OF ALCOHOLS WITH PRIMARY ALKYL-HALIDES IN THE PRESENCE OF SILVER TRIFLATE[J]. TETRAHEDRON LETTERS, 1994, 35 (44) : 8111 - 8112BURK, RM论文数: 0 引用数: 0 h-index: 0机构: Department of Chemical Sciences, Allergan Inc., Irvine, CA 92713GAC, TS论文数: 0 引用数: 0 h-index: 0机构: Department of Chemical Sciences, Allergan Inc., Irvine, CA 92713ROOF, MB论文数: 0 引用数: 0 h-index: 0机构: Department of Chemical Sciences, Allergan Inc., Irvine, CA 92713
- [5] 1,3-SYN DIASTEREOSELECTIVE REDUCTION OF BETA-HYDROXYKETONES UTILIZING ALKOXYDIALKYLBORANES[J]. TETRAHEDRON LETTERS, 1987, 28 (02) : 155 - 158CHEN, KM论文数: 0 引用数: 0 h-index: 0机构: SANDOZ RES INST, E HANOVER, NJ 07936 USA SANDOZ RES INST, E HANOVER, NJ 07936 USAHARDTMANN, GE论文数: 0 引用数: 0 h-index: 0机构: SANDOZ RES INST, E HANOVER, NJ 07936 USA SANDOZ RES INST, E HANOVER, NJ 07936 USAPRASAD, K论文数: 0 引用数: 0 h-index: 0机构: SANDOZ RES INST, E HANOVER, NJ 07936 USA SANDOZ RES INST, E HANOVER, NJ 07936 USAREPIC, O论文数: 0 引用数: 0 h-index: 0机构: SANDOZ RES INST, E HANOVER, NJ 07936 USA SANDOZ RES INST, E HANOVER, NJ 07936 USASHAPIRO, MJ论文数: 0 引用数: 0 h-index: 0机构: SANDOZ RES INST, E HANOVER, NJ 07936 USA SANDOZ RES INST, E HANOVER, NJ 07936 USA
- [6] STEREOSELECTIVE ALDOL CONDENSATIONS VIA BORON ENOLATES[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (11) : 3099 - 3111EVANS, DA论文数: 0 引用数: 0 h-index: 0NELSON, JV论文数: 0 引用数: 0 h-index: 0VOGEL, E论文数: 0 引用数: 0 h-index: 0TABER, TR论文数: 0 引用数: 0 h-index: 0
- [7] AN EFFICIENT TOTAL SYNTHESIS OF (+/-)-BREFELDIN-A[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (25) : 7583 - 7584GREENE, AE论文数: 0 引用数: 0 h-index: 0LEDRIAN, C论文数: 0 引用数: 0 h-index: 0CRABBE, P论文数: 0 引用数: 0 h-index: 0
- [8] New chemical synthesis of the promising cancer chemotherapeutic agent 12,13-desoxyepothilone B: Discovery of a surprising long-range effect on the diastereoselectivity of an aldol condensation[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (30) : 7050 - 7062Harris, CR论文数: 0 引用数: 0 h-index: 0机构: Mem Sloan Kettering Canc Ctr, Bioorgan Chem Lab, New York, NY 10021 USAKuduk, SD论文数: 0 引用数: 0 h-index: 0机构: Mem Sloan Kettering Canc Ctr, Bioorgan Chem Lab, New York, NY 10021 USABalog, A论文数: 0 引用数: 0 h-index: 0机构: Mem Sloan Kettering Canc Ctr, Bioorgan Chem Lab, New York, NY 10021 USASavin, K论文数: 0 引用数: 0 h-index: 0机构: Mem Sloan Kettering Canc Ctr, Bioorgan Chem Lab, New York, NY 10021 USAGlunz, PW论文数: 0 引用数: 0 h-index: 0机构: Mem Sloan Kettering Canc Ctr, Bioorgan Chem Lab, New York, NY 10021 USADanishefsky, SJ论文数: 0 引用数: 0 h-index: 0机构: Mem Sloan Kettering Canc Ctr, Bioorgan Chem Lab, New York, NY 10021 USA
- [9] REGIOSELECTIVE AND STEREOSELECTIVE CROSS-ALDOL REACTIONS VIA DIALKYLBORYL TRIFLATES[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1980, 53 (01) : 174 - 178INOUE, T论文数: 0 引用数: 0 h-index: 0机构: UNIV TOKYO, FAC SCI, DEPT CHEM, BUNKYO KU, TOKYO 113, JAPAN UNIV TOKYO, FAC SCI, DEPT CHEM, BUNKYO KU, TOKYO 113, JAPANMUKAIYAMA, T论文数: 0 引用数: 0 h-index: 0机构: UNIV TOKYO, FAC SCI, DEPT CHEM, BUNKYO KU, TOKYO 113, JAPAN UNIV TOKYO, FAC SCI, DEPT CHEM, BUNKYO KU, TOKYO 113, JAPAN
- [10] Efficient synthesis of the C1-C11 fragment of the tedanolides.: The nonaldol aldol process in synthesis[J]. ORGANIC LETTERS, 2000, 2 (12) : 1669 - 1672Jung, ME论文数: 0 引用数: 0 h-index: 0机构: Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USAMarquez, R论文数: 0 引用数: 0 h-index: 0机构: Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA