Corrigendum to “Synthesis of a key intermediate for the total synthesis of pseudopteroxazole” [Tetrahedron 66 (2010) 1997–2004]

Yadav, J. S.; Bhasker, E. Vijaya; Geetha, V.; Srihari, P.

doi:10.1016/j.tet.2010.04.063

Cited by 2 publications

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“…The stereoselective synthesis of the required acid commenced by acylation of an alkenyl lithium reagent generated from known TES‐protected ( E )‐4‐iodopent‐3‐enol (see above) [18] ( 14 ) with Weinreb amide 15 (Scheme 3 ). [25] …”

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Total Synthesis of Pulvomycin D

Fritz

Wienhold

Hackl

et al. 2021

Chemistry A European J

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A synthetic route to the pulvomycin class of natural products is presented, which culminated in the first synthesis of a pulvomycin, pulvomycin D. Key elements of the strategy include a pivotal aldol reaction which led to bond formation between the C24‐C40 and the C8‐C23 fragment. The remaining C1‐C7 fragment was attached by a Yamaguchi esterification completing the assembly of the 40 carbon atoms within the main skeleton. Ring closure to the 22‐membered lactone ring was achieved in the final stages of the synthesis by a Heck reaction. The completion of the synthesis required the removal of six silyl protecting groups in combination with olefin formation at C26‐C27 by a Peterson elimination.

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confidence: 99%

Total Synthesis of Pulvomycin D

Fritz

Wienhold

Hackl

et al. 2021

Chemistry A European J

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“…如 Scheme 5 所示, 以(＋)-异胡薄荷醇(71)为起始原料, 李昂课题组 [33] 先通过 Mitsunobu 反应得到羟基构型翻转的 72, 再巧妙地利用羟基的导向作用实现硼氢化-氧化的立体化学控制 [36] , 实现对二醇 73 中 C(2)位构型的正确构建. 二异丙基丙炔基氯硅烷(74)顺利实现了 73 中末端羟基的选择性保护 [37] 从 79 出发, 李昂课题组 [33] 又完成了 ileabethoxazole 的不对称全合成(Scheme 6).…”

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Synthetic Progress of Alkaloids against Mycobacterium Tuberculosis: Pseudopteroxazole and Ileabethoxazole

Sun¹,

Xu²,

XiangDong³

2020

Chin. J. Org. Chem.

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Two alkaloids of pseudopteroxazole and ileabethoxazole, isolated from sea whip Pseudopterogorgia elisabethae, have significant antimicrobial activity against pathogen of tuberculosis: Mycobacterium tuberculosis. These two alkaloids possess similar tetracyclic skeleton, which containing four stereocenters, a fully substituted aromatic ring and an uncommon benzoxazole unit in natural products. Significant antimicrobial activity and special molecular structures attracted extensive attentions to synthetic study on pseudopteroxazole and ileabethoxazole. The progress in the total synthesis of these two alkaloids is reviewed. Keywords Mycobacterium tuberculosis; alkaloid; pseudopteroxazole; ileabethoxazole; total synthesis 结核病(Tuberculosis, TB)是由其病原体--结核分枝杆菌(Mycobacterium tuberculosis)经空气传播而引起的传染病. 由于结核分枝杆菌对治疗药物不断突出的耐药性问题, 使得结核病对人类健康的威胁日渐严重. 对结核病的研究已成为一个非常重要和活跃的领域 [1] . 在治疗药物研发中, 具有抗结核分枝杆菌活性的天然产物是筛选优秀先导化合物的一个重要来源 [2][3][4] .Pseudopteroxazole (1) [3] 和 ileabethoxazole (2) [4] 是 Rodriguez 课题组从分别生存于西印度洋和加勒比海中的海鞭 Pseudopterogorgia elisabethae 中分离得到的两种海洋生物碱, 生理活性研究表明两种生物碱对结核分枝杆菌都具有良好的抗菌活性. 两者在分子结构上也颇为相似(图 1), 四环基本骨架中都具有天然产物中少有的苯并噁唑单元(D 环)和一个全取代苯环(A 环), 各自拥有的四个立体中心中有三个完全相同. 不同之处在于 C 环的大小和 C(1)的立体构型以及取代基的不同. 良好的抗结核分枝杆菌活性和独特的分子结构使得对 1 和 2 的全合成研究得到了广泛的关注.

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Corrigendum to “Synthesis of a key intermediate for the total synthesis of pseudopteroxazole” [Tetrahedron 66 (2010) 1997–2004]

Cited by 2 publications

References 0 publications

Total Synthesis of Pulvomycin D

Total Synthesis of Pulvomycin D

Synthetic Progress of Alkaloids against Mycobacterium Tuberculosis: Pseudopteroxazole and Ileabethoxazole

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