Formal synthesis of tubelactomicins via a transannular Diels-Alder approach

被引:10
作者
Anzo, Toshimi [1 ]
Suzuki, Akari [1 ]
Sawamura, Kiyoto [1 ]
Motozaki, Toru [1 ]
Hatta, Madoka [1 ]
Takao, Ken-ichi [1 ]
Tadano, Kin-ichi [1 ]
机构
[1] Keio Univ, Dept Appl Chem, Kohoku Ku, Yokohama, Kanagawa 2238522, Japan
关键词
tubelactomicins; macrolide antibiotics; transannular Diels-Alder reaction; hiyama coupling; ring-closing olefin metathesis;
D O I
10.1016/j.tetlet.2007.10.002
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A formal synthesis of the antimicrobial tricyclic macrolides, tubelactomicins A and E, featured by a transannular Diels-Alder (TADA) approach, has been explored. The key issue for the transannular cyclization was the synthesis of a 24-membered macrolactone equipped with all the requisite functionalities, which has been achieved using an intramolecular Hiyama cross-coupling strategy. The Hiyama coupling reaction spontaneously triggered off the TADA reaction. From the endo-TADA adduct, formal syntheses of tubelactomicins A and E were achieved. The 24-membered macrolactone formation was also achieved via an intramolecular ring-closing metathesis approach. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:8442 / 8448
页数:7
相关论文
共 20 条
[1]   THE DIELS-ALDER ROUTE TO ALLYLSILANES FROM 1-TRIMETHYLSILYLBUTADIENES [J].
CARTER, MJ ;
FLEMING, I ;
PERCIVAL, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (09) :2415-2434
[2]   (E)-3-(TRIMETHYLSILYL)-2-PROPEN-1-OL - AN IMPROVED PREPARATION [J].
DENMARK, SE ;
JONES, TK .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (23) :4595-4597
[3]   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
[4]   A user-friendly entry to 2-iodoxybenzoic acid (IBX) [J].
Frigerio, M ;
Santagostino, M ;
Sputore, S .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (12) :4537-4538
[5]  
Grubbs R.H., 2003, HDB METATHESIS, V3
[6]  
Hiyama T, 1998, METAL-CATALYZED CROSS-COUPLING REACTIONS, P421
[7]   Total synthesis of an antitubercular lactone antibiotic, (+)-tubelactomicin A [J].
Hosokawa, S ;
Seki, M ;
Fukuda, H ;
Tatsuta, K .
TETRAHEDRON LETTERS, 2006, 47 (14) :2439-2442
[8]   Tubelactomicin A, a novel 16-membered lactone antibiotic, from Nocardia sp.: I.: Taxonomy, production, isolation and biological properties [J].
Igarashi, M ;
Hayashi, C ;
Homma, Y ;
Hattori, S ;
Kinoshita, N ;
Hamada, M ;
Takeuchi, T .
JOURNAL OF ANTIBIOTICS, 2000, 53 (10) :1096-1101
[9]   Tubelactomicin A, a novel 16-membered lactone antibiotic, from Nocardia sp.: II.: Structure elucidation [J].
Igarashi, M ;
Nakamura, H ;
Naganawa, H ;
Takeuchi, T .
JOURNAL OF ANTIBIOTICS, 2000, 53 (10) :1102-1107
[10]   AN IMPROVED PROCEDURE FOR THE PREPARATION OF THE DESS-MARTIN PERIODINANE [J].
IRELAND, RE ;
LIU, LB .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (10) :2899-2899