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Si us plau utilitzeu sempre aquest identificador per citar o enllaçar aquest document: https://hdl.handle.net/2445/227643
Ring-closing metathesis studies in the context of the formal synthesis of themarine macrolide (–)-callyspongiolide
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Attempts to synthesize the natural product macrolide polyketide (–)-callyspongiolide have drawn great interest
because of its potent cytotoxic activity. Its total synthesis has proven to be difficult, however, due to its
challenging structure. The influence of the configuration of a homoallylic stereocenter on the closure of a 14-
membered macrocyclic carbonate by ring-closing metathesis (RCM) from two epimeric dienes is described. The
results offer some insights into the structural features which contribute to hampering the closure of the
macrocyclic core of the macrolide polyketide. A formal synthesis of the marine macrolide (–)-callyspongiolide is
also reported using a RCM approach (C10-C11 bond formed) from analogous dienes bearing an α,β-unsaturated
ester instead of a carbonate
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URBINA, Andrea, et al. Ring-closing metathesis studies in the context of the formal synthesis of themarine macrolide (–)-callyspongiolide. Arkivoc. 2025. ISSN 1551-7012. [consulted: 9 of June of 2026]. Available at: https://hdl.handle.net/2445/227643