Germacrene B – a central intermediate in sesquiterpene biosynthesis

• Houchao Xu and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2023, 19, 186–203, doi:10.3762/bjoc.19.18

• farnesylfarnesyl diphosphate (FFPP) can serve as a precursor to triterpenes [5], a compound class that was believed to be solely derived from squalene. Terpene synthases convert these linear precursors through cationic cascade reactions into terpene hydrocarbons or alcohols [6][7][8]. For type I terpene synthases

Enzymes in biosynthesis

• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2022, 18, 1131–1132, doi:10.3762/bjoc.18.116

• geranylgeranyl diphosphate, into sesqui- or diterpenes, respectively. As has been described recently, even farnesylfarnesyl diphosphate can be converted into triterpenes, a substance class that was previously believed to originate exclusively from squalene by class II terpene synthases [1]. These conversions

The direct oxidative diene cyclization and related reactions in natural product synthesis

• Juliane Adrian,
• Leona J. Gross and
• Christian B. W. Stark

Beilstein J. Org. Chem. 2016, 12, 2104–2123, doi:10.3762/bjoc.12.200

• oxide (79) in a further few steps. Teurilene Teurilene (82) is a squalene-derived cytotoxic polyether which was originally extracted from the red algae Laurencia obtusa by Suzuki et al. [138][139]. Though it is CS-symmetric, it is structurally closely related to pentacyclic C2-symmetric glabrescol [140

Synthesis of a deuterated probe for the confocal Raman microscopy imaging of squalenoyl nanomedicines

• Eric Buchy,
• Branko Vukosavljevic,
• Maike Windbergs,
• Dunja Sobot,
• Camille Dejean,
• Simona Mura,
• Patrick Couvreur and
• Didier Desmaële

Beilstein J. Org. Chem. 2016, 12, 1127–1135, doi:10.3762/bjoc.12.109

• -Sud, 5, rue Jean-Baptiste Clément, 92296 Châtenay-Malabry, France 10.3762/bjoc.12.109 Abstract The synthesis of ω-di-(trideuteromethyl)-trisnorsqualenic acid has been achieved from natural squalene. The synthesis features the use of a Shapiro reaction of acetone-d6 trisylhydrazone as a key step to

• : deuterium labelling; nanomedicine; Raman spectroscopy; Shapiro reaction; squalene; Introduction Application of nanotechnology to medicine holds promises to profoundly impact healthcare especially to treat severe diseases such as cancer, intracellular infections, neurodegenerative diseases, etc. Indeed, the

• developed covering all aspects of medicine. Among them, lipid drug conjugates (LDC) were especially developed for the delivery of hydrophilic drugs by covalent coupling with lipid components [3][4]. In this context we recently found that the chemical conjugation of squalene, a natural and biocompatible

Application of cyclic phosphonamide reagents in the total synthesis of natural products and biologically active molecules

• Thilo Focken and
• Stephen Hanessian

Beilstein J. Org. Chem. 2014, 10, 1848–1877, doi:10.3762/bjoc.10.195

• , respectively, and subsequent conversion of the primary adducts [35]. The enantioselective synthesis of α-phosphonosulfonic acids as squalene inhibitors, as discussed later in this review, was achieved using similar reactions – asymmetric alkylation of an α-sulfo phosphonamide and asymmetric α-sulfuration of an

• phosphonamide 67. A similar displacement reaction was used to generate a phosphonamide reagent in the synthesis of squalene synthase inhibitors [36] and is discussed later in this review. Phosphonamides by alkylation of phosphorus acid diamides Spilling and co-workers reported the preparation of alkyl

• the formed lactol with Fetizon’s reagent afforded 94. The final steps of the synthesis involved conversion to the corresponding α,β-unsaturated lactone 95 and modification of the side chain to re-build the original double bond to eventually give (+)-acetoxycrenulide (10) [41][42]. Squalene synthase