The isolation and synthesis of neodolastane diterpenoids

Abstract

The neodolastane diterpenoids comprise a group of 44 compounds including guanacastepenes, heptemerones, plicatilisins, radianspenes, 2,15-epoxy-5,13-dihydroxyneodolast-3-en-14-one and sphaerostanol. These fungal and marine natural products are characterized by a tricyclic neodolastane skeleton that consists of fused five-, seven- and six-membered rings. Their reported antibiotic activities against antibiotic-resistant bacteria together with strong antifungal and anticancer activities and their novel structures render these compounds interesting synthetic targets. The aim of this account is to summarise the progress in the isolation, characterisation and synthesis of these diterpenoids as well as to review their biogenetic origins and diverse biological activities since their discovery in 2000.

Secondary Metabolites Isolated from Tricholoma Species (Basidiomycota, Tricholomatacee): A Review

“…Biogenetically the trichoaurantianes (seconeodolastanes) have been considered to derive by oxidative cleavage of the six-membered ring of the neodolastane (guanacastane) skeleton [9], which is the characteristic carbon backbone of several diterpenoids isolated from several mushrooms of the genus Coprinus and Trametes [16]. The neodolastane structure possibly arises from a dolabellane precursor which is converted either to a neodolabellane or to a dolastane-type diterpenoid by a different timing of the six-membered ring closure between C-2 and C-7 and the Wagner-Meerwein migration of the methyl group from C-11 to C-10 ( Figure 1) [9].…”

“…In addition to saponaceolides A (11) and B (12), three new saponaceolides, E (15), F (16), and G (17) were later isolated from samples of T. saponaceum collected in Japan [20]. Compound 15 is the geometric isomer of saponaceolide A (11) at the C(8)C(9) double bond; however, the configuration of the hydroxyl group at C(10) remains undetermined.…”

Assembly of Terpenoid Cores by a Simple, Tunable Strategy

“…Deconjugative alkylation (to 13 a–b ) with furfuryl bromide followed by intramolecular Diels–Alder furan (IMDAF) cycloaddition yields the tricyclic frameworks 14 a–14 b . Although the cycloaddition yields are modest, this has the potential to be a simple approach to diterpenoid natural product analogs related to icetexane and neodolastane families.…”

Three new diterpenoids from Marrubium aschersonii

“…Their fascinating structures and extensive biological activities have attracted broad interests from both natural products and synthetic chemists (Farooq et al, 2015;Hanson, 2015;Markovi c et al, 2015). The genus Marrubium (Lamiaceae) comprising about 40 species is mainly distributed in Europe, North Africa, and Asia (Meyre-Silva and Cechinel-Filho, 2010;Mabberley, 1997).…”