Total Synthesis of Auripyrones A and B and Determination of the Absolute Configuration of Auripyrone B

被引:19
|
作者
Hayakawa, Ichiro [1 ]
Takemura, Takuma [1 ]
Fukasawa, Emi [1 ]
Ebihara, Yuta [1 ]
Sato, Natsuki [1 ]
Nakamura, Takayasu [1 ]
Suenaga, Kiyotake [1 ]
Kigoshi, Hideo [1 ]
机构
[1] Univ Tsukuba, Dept Chem, Grad Sch Pure & Appl Sci, Tsukuba, Ibaraki 3058571, Japan
关键词
aldol reactions; auripyrones; diastereoselectiyity; natural products; total synthesis; NATURAL-PRODUCTS; ALDOL REACTIONS; METABOLITES;
D O I
10.1002/anie.200906662
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Figure Presented) The winner takes it aldol: The total synthesis of auripyrones A and B was achieved using a diastereoselective aldol-type reaction with 2, 6-diethyl-3, 5-dimethyl-4-pyrone as a key step. The stereostructure and absolute configura-tion of auripyrone B has also been determined. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:2401 / 2405
页数:5
相关论文
共 50 条
  • [31] Total Synthesis and Absolute Configuration of Simpotentin, a Potentiator of Amphotericin B Activity
    Ohtawa, Masaki
    Shimizu, Eri
    Saito, Atsushi
    Sakamoto, Sayuri
    Waki, Ai
    Kondo, Ariko
    Yagi, Akiho
    Uchida, Ryuji
    Tomoda, Hiroshi
    Nagamitsu, Tohru
    ORGANIC LETTERS, 2019, 21 (14) : 5596 - 5599
  • [32] Total synthesis and absolute configuration of simpotentin, a potentiator of amphotericin B activity
    Ohtawa, Masaki
    Uchida, Ryuji
    Tomoda, Hiroshi
    Nagamitsu, Tohru
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 258
  • [33] Total Synthesis and Absolute Configuration of the Bisanthraquinone Antibiotic BE-43472B
    Nicolaou, K. C.
    Lim, Yee Hwee
    Becker, Jochen
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (19) : 3444 - 3448
  • [34] Total Synthesis and Determination of the Absolute Configuration of Shodoamide C: An Amphotericin B Potentiator against Candida albicans
    Ueki, Shogo
    Hirata, Akihiro
    Yagi, Akiho
    Iwahori, Masahiro
    Tomoda, Hiroshi
    Uchida, Ryuji
    Nagamitsu, Tohru
    Ohtawa, Masaki
    ORGANIC LETTERS, 2025,
  • [35] Synthesis and absolute configuration of (+)-hyperolactone B
    Ueki, T.
    Ichinari, D.
    Yoshihara, K.
    Morimoto, Y.
    Tetrahedron Letters, 39 (07):
  • [36] Synthesis and absolute configuration of (+)-hyperolactone B
    Ueki, T
    Ichinari, D
    Yoshihara, K
    Morimoto, Y
    Kinoshita, T
    TETRAHEDRON LETTERS, 1998, 39 (07) : 667 - 668
  • [37] Total synthesis of auripyrone A
    Lister, T
    Perkins, MV
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (16) : 2560 - 2564
  • [38] Total synthesis of (-)-galbonolide B and the determination of its absolute stereochemistry
    Tse, B
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (30) : 7094 - 7100
  • [39] Total synthesis of (-)-stellettamide B and determination of its absolute stereochemistry
    Yamazaki, N
    Dokoshi, W
    Kibayashi, C
    ORGANIC LETTERS, 2001, 3 (02) : 193 - 196
  • [40] Determination of the absolute configuration of the diterpene tonantzitlolone B
    Busch, Torsten
    Schuster, Hannah
    Kirschning, Andreas
    TETRAHEDRON LETTERS, 2008, 49 (36) : 5273 - 5275