Total Synthesis of Aigialomycin D using a One-Pot Ketene Generation-Trapping-Aromatization Sequence

被引:56
作者
Calo, Frederick [1 ]
Richardson, Jeffery [2 ]
Barrett, Anthony G. M. [1 ]
机构
[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England
[2] Eli Lilly & Co Ltd, Windlesham GU20 6PH, Surrey, England
基金
英国工程与自然科学研究理事会;
关键词
ENANTIOSELECTIVE TOTAL-SYNTHESIS; RING-CLOSING METATHESIS; NATURAL-PRODUCTS; ACID; MACROCYCLIZATION;
D O I
10.1021/ol901979x
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The total synthesis of aigialomycin D, without the need for phenol protection, was carried out using the C-acylation of a keto-dioxinone dianion, a cascade sequence consisting of ketene generation, alcohol trapping and aromatization, and ring-closing metathesis.
引用
收藏
页码:4910 / 4913
页数:4
相关论文
共 28 条
[1]   Total Synthesis of Aigialomycin D Using a Ramberg-Backlund/RCM Strategy [J].
Baird, Lynton J. ;
Timmer, Mattie S. M. ;
Teesdale-Spittle, Paul H. ;
Harvey, Joanne E. .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (06) :2271-2277
[2]   Syntheses of epi-aigialomycin D and deoxy-aigialomycin C via a diastereoselective ring closing metathesis macrocyclization protocol [J].
Bajwa, Naval ;
Jennings, Michael P. .
TETRAHEDRON LETTERS, 2008, 49 (02) :390-393
[3]   Modular asymmetric synthesis of aigialomycin D, a kinase-inhibitory scaffold [J].
Barluenga, Sofia ;
Dakas, Pierre-Yves ;
Terandin, Yoan ;
Meijer, Laurent ;
Winssinger, Nicolas .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (24) :3951-3954
[4]   AN ACYL RADICAL INITIATED TANDEM 7-ENDO/5-EXO RADICAL CYCLIZATION APPROACH TO ENANTIOMERICALLY PURE BICYCLO[5.3.0]DECAN-2-ONES [J].
BATTY, D ;
CRICH, D .
TETRAHEDRON LETTERS, 1992, 33 (07) :875-878
[5]   AN ENANTIOSELECTIVE AND HIGHLY CONVERGENT SYNTHESIS OF (+)-IKARUGAMYCIN [J].
BOECKMAN, RK ;
WEIDNER, CH ;
PERNI, RB ;
NAPIER, JJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (20) :8036-8037
[6]   Toward the development of a general chiral auxiliary. A total synthesis of (+)-tetronolide via a tandem ketene-trapping [4+2] cycloaddition strategy [J].
Boeckman, Robert K., Jr. ;
Shao, Pengcheng ;
Wrobleski, Stephen T. ;
Boehmler, Debra J. ;
Heintzelman, Geoffrey R. ;
Barbosa, Antonio. J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (32) :10572-10588
[7]   Total synthesis of aigialomycin D: Surprising chemoselectivity dependence on alkyne structure in nickel-catalyzed cyclizations [J].
Chrovian, Christa C. ;
Knapp-Reed, Beth ;
Montgomery, John .
ORGANIC LETTERS, 2008, 10 (05) :811-814
[8]  
DERUYTTERE X, 1992, SYNLETT, P51
[9]   A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES [J].
DESS, DB ;
MARTIN, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7277-7287
[10]  
FELDMAN PL, 1984, J ORG CHEM, V49, P5105