The sponge-derived macrolide (-)-dictyostatin (1) has been reported to exhibit paclitaxel-like effects on cellular microtubules and to inhibit human cancer cell proliferation (even of paclitaxel-resistant cancer cell lines) at low nanomolar concentrations, with activity somewhat superior to the already very active discodermolide. Although four total syntheses of (-)-dictyostatin were recently completed, the development of a practical and flexible synthesis remains an important goal, particularly as its natural supply is extremely scarce. Here we report a highly stereoselective synthesis of the C1–C26 (2), the C10-C26 (3) and the C1–9 (4) fragments of (-)-dictyostatin. Work is in progress to complete the total synthesis of (-)-dictyostatin.
Approaches to the Stereoselective Total Synthesis of (-)-Dictyostatin / C. Zanato, L.L. Pignataro, Z. Hao, C.M.A. Gennari. ((Intervento presentato al 34. convegno Corso Estivo Attilio Corbella : Seminari di Sintesi Organica tenutosi a GARGNANO (BS) nel 2009.
Approaches to the Stereoselective Total Synthesis of (-)-Dictyostatin
C. ZanatoPrimo
;L.L. PignataroSecondo
;C.M.A. GennariUltimo
2009
Abstract
The sponge-derived macrolide (-)-dictyostatin (1) has been reported to exhibit paclitaxel-like effects on cellular microtubules and to inhibit human cancer cell proliferation (even of paclitaxel-resistant cancer cell lines) at low nanomolar concentrations, with activity somewhat superior to the already very active discodermolide. Although four total syntheses of (-)-dictyostatin were recently completed, the development of a practical and flexible synthesis remains an important goal, particularly as its natural supply is extremely scarce. Here we report a highly stereoselective synthesis of the C1–C26 (2), the C10-C26 (3) and the C1–9 (4) fragments of (-)-dictyostatin. Work is in progress to complete the total synthesis of (-)-dictyostatin.Pubblicazioni consigliate
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