Total Synthesis of (-)-Sacidumlignans B and D

被引:24
|
作者
Rout, Jeetendra Kumar [1 ]
Ramana, C. V. [1 ]
机构
[1] Natl Chem Lab CSIR NCL, Pune 411008, Maharashtra, India
来源
JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 03期
关键词
IODOXYBENZOIC ACID IBX; ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; ALCOHOLS; CLEAVAGE; MAGNOSHININ; REDUCTION; REAGENT; DECOMPOSITION; DERIVATIVES;
D O I
10.1021/jo2021696
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first total synthesis of naturally occurring sacidumlignans A (1), B (2), and D (4) was executed and the absolute configuration of 2 and 4 was determined. A diastereoselective alpha- methylation of a lactone was used as the key step for the control of the chiral centers of the central lignan core. An acid mediated dehydrative cyclization of an aldehyde to construct the dihydronaphthalene unit of 2 and the aromatization of the intermediate dihydronaphthalene derivative to synthesize 1 are the key reactions employed in this regard.
引用
收藏
页码:1566 / 1571
页数:6
相关论文
共 50 条
  • [1] Total synthesis of (±)-sacidumlignans D and A through Ueno-Stork radical cyclization reaction
    Zhang, Jian-Jian
    Yan, Chang-Song
    Peng, Yu
    Luo, Zhen-Biao
    Xu, Xiao-Bo
    Wang, Ya-Wen
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (15) : 2498 - 2513
  • [2] Total Synthesis of Aculenes B and D
    Yokokawa, Hinata
    Ishizawa, Seiya
    Saito, Katsuya
    Meguro, Yasuhiro
    Kuwahara, Shigefumi
    Enomoto, Masaru
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (06)
  • [3] Total synthesis of topopyrones B and D
    Tan, Jason Samuel
    Ciufolini, Marco A.
    ORGANIC LETTERS, 2006, 8 (21) : 4771 - 4774
  • [4] Total Synthesis of Alternatamides B and D
    Wu, Bo-You
    Lin, Cheng-Kun
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 13 (06)
  • [5] Total synthesis of nitropyrrolins A, B, and D
    Mitani, Hikaru
    Matsuo, Tomoki
    Kodama, Takeshi
    Nishikawa, Keisuke
    Tachi, Yoshimitsu
    Morimoto, Yoshiki
    TETRAHEDRON, 2016, 72 (45) : 7179 - 7184
  • [6] Total synthesis of epothilones B and D
    Taylor, RE
    Chen, Y
    ORGANIC LETTERS, 2001, 3 (14) : 2221 - 2224
  • [7] First total synthesis of Artekeiskeanol B and D
    Ranganath, P. L. N.
    Annapurna, K.
    Anil, T.
    Narsaiah, A. Venkat
    ARKIVOC, 2022, : 114 - 125
  • [8] The total synthesis of coleophomones B, C, and D
    Nicolaou, KC
    Montagnon, T
    Vassilikogiannakis, G
    Mathison, CJN
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (24) : 8872 - 8888
  • [9] Total synthesis of koninginin D, B and E
    Liu, G
    Wang, ZQ
    SYNTHESIS-STUTTGART, 2001, (01): : 119 - 127
  • [10] Total Synthesis of Taiwaniadducts B, C, and D
    Deng, Jun
    Zhou, Shupeng
    Zhang, Wenhao
    Li, Jian
    Li, Ruofan
    Li, Ang
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (23) : 8185 - 8188