Natural sesquiterpenoids

Abstract

This review covers the isolation, structural determination, synthesis and chemical and microbiological transformations of natural sesquiterpenoids. 421 references are cited.

Synthetic Studies towards Guaianolide Sesquiterpene Lactones

“…[10] ). Major isomer: 1 Supporting Information (see footnote on the first page of this article): Experimental procedures and characterization data for 5, 8 and 9, crystallographical and computational study of the hydrogen bonds in 4, computational study of the hydrogen bond in 7, copies of 1 H and 13 C NMR spectra for 5 and the two diastereomers of 9.…”

“…Guaianolides, of which compounds 1 and 2 are the archetype (Figure 1),3 are by far the most common sesquiterpene lactones (STLs) in natural products with this bicyclic framework. They usually exhibit a trans ‐γ‐lactone ring fused to the C 6 –C 7 bond of the bicycle or, less often, to the C 7 –C 8 bond, and have been the subject of considerable synthetic4 and biological studies 1,5. In our continuous effort towards eco‐compatible synthetic routes to valuable molecules involving domino and/or multicomponent reactions (MCRs), we have recently developed the MARDi cascade, a Michael‐initiated MCR which allows a diastereoselective access to a variety of carbo‐ and heterocyclic seven‐membered rings under user‐ and environmentally friendly conditions 6.…”

“…The bicyclo [5.3.0]decane ring system is present in numerous classes of naturally occurring sesquiterpenes [1] and diterpenes. [2] Guaianolides, of which compounds 1 and 2 are the archetype (Figure 1), [3] are by far the most common sesquiterpene lactones (STLs) in natural products with this bicyclic framework.…”

“…They usually exhibit a trans-γ-lactone ring fused to the C 6 -C 7 bond of the bicycle or, less often, to the C 7 -C 8 bond, and have been the subject of considerable synthetic [4] and biological studies. [1,5] In our continuous effort towards eco-compatible synthetic routes to valuable molecules involving domino and/or multicomponent reactions (MCRs), we have recently developed the MARDi cascade, a Michael-initiated MCR which allows a diastereoselective access to a variety of carbo-and heterocyclic seven-membered rings under user-and environmentally friendly conditions. [6] The application of multicomponent/ domino reactions [7] to target-oriented synthesis has been conceptualized as early as 1917 by Robinson, and its advantages have been demonstrated with the efficient one-pot synthesis of the bridged bicyclic alkaloid tropinone by using a double Mannich three-component reaction.…”

Ribosomal peptide natural products: bridging the ribosomal and nonribosomal worlds

“…156–160 In primary metabolism, it is also critical to normal cellular functions, such as protein farnesylation and gernanylgeranylation 161–164. There are two families of prenylated RPs in the literature.…”