Total Synthesis of Notoamides F, I, and R and Sclerotiamide

Zhang, Benxiang; Wei, Zheng; Wang, Xiaoqing; Sun, Deqian; Li, Chaozhong

doi:10.1002/anie.201604754

Cited by 65 publications

(38 citation statements)

References 39 publications

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“…218 The indole alkaloids notoamides F and R (Aspergillus sp., mussel Mytilus edulis galloprovincialis) and the related spirooxindole (À)-sclerotiamide, have been synthesised in a convergent manner from commercially available Seebach acetal. 219 A rst synthesis of notoamide I was also claimed 219 but the synthesis had already been reported. 220 Denrodolides C and D (Dendrodochium sp., sea cucumber Holothuria nobilis) have been prepared from commercially available materials.…”

Section: Marine-sourced Bacteriamentioning

confidence: 99%

Marine natural products

et al. 2018

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Covering: 2016. Previous review: Nat. Prod. Rep., 2017, 34, 235-294This review covers the literature published in 2016 for marine natural products (MNPs), with 757 citations (643 for the period January to December 2016) referring to compounds isolated from marine microorganisms and phytoplankton, green, brown and red algae, sponges, cnidarians, bryozoans, molluscs, tunicates, echinoderms, mangroves and other intertidal plants and microorganisms. The emphasis is on new compounds (1277 in 432 papers for 2016), together with the relevant biological activities, source organisms and country of origin. Reviews, biosynthetic studies, first syntheses, and syntheses that led to the revision of structures or stereochemistries, have been included.

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Section: Marine-sourced Bacteriamentioning

confidence: 99%

Marine natural products

et al. 2018

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“…Li, Sun, and co‐workers reported the total synthesis of notoamides F ( 186 ), I ( 184 ), and R ( 185 ), members of the prenylated indole alkaloid family, as well as sclerotiamide ( 187 ), biosynthetically related to notoamide R . Their strategy was based on an oxidative aza‐Prins cyclization to construct the bicyclo[2.2.2]diazaoctane ring, starting from the dipeptide derivative 181 .…”

Section: Synthesis Of Natural Products and Bioactive Moleculesmentioning

confidence: 99%

The Aza‐Prins Reaction in the Synthesis of Natural Products and Analogues

et al. 2017

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International audienceThe classical Prins cyclization reaction has been one of the most studied reactions during the last two decades and it has found many applications in key steps of natural product syntheses, especially for products containing pyran units and related structures in their core skeletons. The nitrogen-based version of the Prins reaction, aza-Prins cyclization, has found its own relevance in organic synthesis owing to the fact that it gives direct access to piperidines, which are even more widespread in natural products and in drugs. Even though the potential scope of the reaction is vast, and despite it having afforded significant progress in the synthesis of various azaheterocycles, its applications in the field of natural product synthesis is massively underdeveloped in comparison with the classical Prins reaction. A compilation of the applications of azaPrins cyclization in the preparation of natural products and selected analogues, especially compounds of potential biological interest, is presented, with emphasis placed on the key roles of this reaction in the total synthesis of these products

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“…1B). [5][6][7][8] Despite the existing elegant strategies to access specic congeners within this family of natural products, a unied approach to access prenylated indole alkaloids that either possess or lack additional substituents on the cyclic amine ring (highlighted in maroon in Fig. 2A and labelled ring A in Fig.…”

Section: Introductionmentioning

confidence: 99%