From synthetic control to natural products: a focus on N‐heterocycles

Abstract

Natural products containing a N‐heterocycle motif are widespread in nature and medicinal plants, in particular, have proved to be a source of almost unlimited N‐derived structures with high molecular diversity. Because of their intrinsic potential for use in both biomedical and agricultural applications, there is a general need for new compounds and for the synthesis of ‘natural‐inspired’ analogues. Importantly, transition of a natural product from discovery to a ‘market lead’ is associated with an increasingly challenging demand for more of the compound, which cannot be met by isolation from natural plant sources, often due to low extraction yields and uneven availability of the plant source itself. Synthesis remains the most reliable approach to provide valuable products for the market. In this review, a comprehensive overview of our contribution to synthetic access to N‐derived natural products is given. Major strengths of the proposed methodologies are discussed critically. © 2019 Society of Chemical Industry

Visible-Light-Induced Formation of Thiavinyl 1,3-Dipoles: A Metal-Free [3+2] Oxidative Cyclization with Alkynes as Easy Access to Thiophenes

“…H eterocyclizations are powerful tools for the synthesis of five-membered heterocycles 1−4 that are often found in natural products 5,6 and synthetic pharmaceuticals 7−9 and widely used in material science and organic synthesis. 10−17 Recent studies revealed that oxidative heterocyclizations 18−21 could evoke novel and useful catalytic transformations, which otherwise are difficult to achieve.…”

“…Heterocyclizations are powerful tools for the synthesis of five-membered heterocycles − that are often found in natural products , and synthetic pharmaceuticals − and widely used in material science and organic synthesis. − Recent studies revealed that oxidative heterocyclizations − could evoke novel and useful catalytic transformations, which otherwise are difficult to achieve. For example, the cyclization of ketene dithioacetals, − a kind of electron-rich olefin, under electrochemical conditions afforded the cyclic amino acid derivatives (Scheme a, X = NH) .…”

Stereocontrolled Synthesis of Some Novel Azaheterocyclic β-Amino Ester Stereoisomers with Multiple Stereogenic Centers

“…Azaheterocycles are highly abundant structural elements in natural products, drugs, and other bioactive molecules (Figure 1 ). 9 10 11 As a consequence, the synthesis of functionalized azaheterocycles remains a highlighted topic in medicinal chemistry and there is a constant need to develop novel methods. 5,11…”

“…[6][7][8] Scheme 1 General mechanisms for ring-rearrangement metathesis Azaheterocycles are highly abundant structural elements in natural products, drugs, and other bioactive molecules (Figure 1). [9][10][11] As a consequence, the synthesis of functionalized azaheterocycles remains a highlighted topic in medicinal chemistry and there is a constant need to develop novel methods. 5,11 Azaheterocyclic -amino acids are an interesting subgroup of this compound family.…”

2019 – A year of continued growth

“…The use of biopesticides in underdeveloped countries was reviewed by Srinivasan et al . There was a more focused review on natural N ‐heterocyclic compounds as leads for pesticides . The use of strigolactones for parasitic weed management and the use of alleopathy for weed management in general were updated .…”