Steroids: partial synthesis in medicinal chemistry

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

“…A common strategy to circumvent this issue is to employ a cyclization strategy that commences from a D-ring precursor already containing the correct stereochemistry at the future CD ring junction [153–154]. Linclau and co-workers developed this concept further and a general steroid construction strategy based on the formation of a D-ring template that contains the correct configuration of three stereocenters C8, C13 and C14 with suitable functionalization for the following C- and B-ring cyclizations (Fig.…”

Novel Steroidal 5α,8α-Endoperoxide Derivatives with Semicarbazone/Thiosemicarbazone Side-chain as Apoptotic Inducers through an Intrinsic Apoptosis Pathway: Design, Synthesis and Biological Studies

“…The interesting structural and stereochemical features of the steroid nucleus provide system and side chains [13]. The interesting structural and stereochemical features of the steroid nucleus provide additional fascination for researchers, and the introduction of heteroatoms, heterocycles, or amides, or replacement of one or more carbon atoms in the steroidal skeleton has been envisaged to discover new chemical entities with the potential to become promising future drugs, resulting in notable modifications in biological activity [14][15][16]. Ergosterol peroxide (5α,8α-epidioxiergosta-6,22-dien-3β-ol, EP) is a member of a class of fungal secondary metaboliters of sterol 5α,8α-endoperoxidederivatives ( Figure 2).…”

“…Ergosterol peroxide (5α,8α-epidioxiergosta-6,22-dien-3β-ol, EP) is a member of a class of fungal secondary metaboliters of sterol 5α,8α-endoperoxidederivatives ( Figure 2). A number of biological activities have been attributed to EP, including antitumor, anti-inflammatory, antiviral and immunomodulatory activities and antioxidant activities [16][17][18][19][20][21]. As an important active lead compound in drug discovery, EP is well known for its 5α,8α-peroxy moiety.…”

Total synthesis of steroids and heterosteroids from BISTRO

“…Efforts in steroids total synthesis have never stopped [4,5]. Yet, according to the Monthly Index of Medical Specialities (UK) [6], one third of the drugs available listed either are or contain steroids and 10,000 structures are listed in the Dictionary of Steroids (according to the Beilstein library, close to 100,000 steroids are known) [7].…”