Concise Syntheses of Violaceoids A and C

被引：4
|
作者：
Narita, Koichi [1 ]
Kimura, Ryuhei [1 ]
Satoh, Hiroka [1 ]
Watanabe, Kazuhiro [1 ]
Yoshimura, Yuichi [1 ,2 ]
机构：
[1] Tohoku Med & Pharmaceut Univ, Fac Pharmaceut Sci, Lab Synthet & Med Chem, Aoba Ku, 4-4-1 Komatsushima, Sendai, Miyagi 9818558, Japan
[2] Tohoku Med & Pharmaceut Univ, Fac Pharmaceut Sci, Lab Organ & Pharmaceut Chem, Aoba Ku, 4-4-1 Komatsushima, Sendai, Miyagi 9818558, Japan
来源：
CHEMICAL & PHARMACEUTICAL BULLETIN | 2021年 / 69卷 / 02期
基金：
日本学术振兴会;
关键词：
violaceoid; alkylated hydroquinone; protecting-group-free synthesis; total synthesis; EFFICIENT SYNTHESIS; ALDEHYDES; PHENOLS;
D O I：
10.1248/cpb.c20-00816
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
The concise syntheses of two alkylated hydroquinone natural products, violaceoids A and C, were accomplished by a protecting-group-free method employing the commercially available 2,5-dihydroxybenzaldehyde as the starting material. The key strategy of the syntheses is the utilization of alkenylboronic acid as both the coupling and temporary protective reagents to efficiently introduce the requisite alkenyl side chain of violaceoid A. Moreover, the synthesis of violaceoid C is reported here for the first time.
引用
收藏
页码：232 / 235
页数：4
相关论文
共 50 条
  • [41] SYNTHESES OF ARYLTETRALIN LIGNANS - CONCISE SYNTHESES OF (+/-)-ISOPODOPHYLLOTOXONE, (+/-)-PICROPODOPHYLLONE AND THEIR RELATED-COMPOUNDS
    OGIKU, T
    YOSHIDA, S
    KURODA, T
    TAKAHASHI, M
    OHMIZU, H
    IWASAKI, T
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1992, 65 (12) : 3495 - 3497
  • [42] Concise syntheses of coronarin A, coronarin E, austrochaparol and pacovatinin A
    Miyake, Takahiro
    Uda, Keisuke
    Kinoshita, Masako
    Fuji, Mikio
    Akita, Hiroyuki
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2008, 56 (03) : 398 - 403
  • [43] Concise and Stereoselective Total Syntheses of Annotinolides C, D, and E (vol 143, pg 11951, 2021)
    Qu, Pei
    Snyder, Scott A.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (41) : 17300 - 17301
  • [44] Concise total syntheses of the sesquiterpenoids (-)-homalomenol A and (-)-homalomenol B
    Piers, E
    Oballa, RM
    JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (24): : 8439 - 8447
  • [45] Concise Syntheses and Biological Activities of Ganomycin I and Fornicin A
    Yajima, Arata
    Urao, Shota
    Katsuta, Ryo
    Nukada, Tomoo
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (04) : 731 - 738
  • [46] Concise syntheses of three ω-3 polyunsaturated fatty acids
    Jakobsen, Martin Gjerde
    Vik, Anders
    Hansen, Trond Vidar
    TETRAHEDRON LETTERS, 2012, 53 (44) : 5837 - 5839
  • [47] Concise Syntheses of (-)-11-O-Debenzoyltashironin and (-)-Bilobalide
    Ohtawa, Masaki
    Shenvi, Ryan A.
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2022, 80 (08) : 766 - 777
  • [48] Concise total syntheses of lysergene, lysergine, isolysergine and festuclavine
    Tasker, Nikhil R.
    Wipf, Peter
    ARKIVOC, 2024, : 1 - 13
  • [49] Concise total syntheses of variolin B and deoxyvariolin B
    Anderson, RJ
    Hill, JB
    Morris, JC
    JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (16): : 6204 - 6212
  • [50] Concise asymmetric syntheses of (-)-lentiginosine and of its pyrrolizidinic analogue
    Ayad, T
    Génisson, Y
    Baltas, M
    Gorrichon, L
    CHEMICAL COMMUNICATIONS, 2003, (05) : 582 - 583
12345