Get Metathesis in Natural Product Synthesis: Strategies, PDF

By Janine Cossy, Stellios Arseniyadis, Christophe Meyer, Robert H. Grubbs

ISBN-10: 3527324402

ISBN-13: 9783527324408

Emphasizing the effect of metathesis in average product synthesis throughout the types of key reactions, this can be a entire view of a sizzling subject. Written via best foreign authors, this prepared reference is obviously established and full of very important info, together with consultant experimental techniques for useful applications.A genuine must-have for a person operating in traditional product synthesis.

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Additional info for Metathesis in Natural Product Synthesis: Strategies, Substrates and Catalysts

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Eight to ten-membered-rings, which are common in natural products [35], can be prepared by heterolytic fragmentation of bicyclic systems [36]. The latter can be formed by several methods among which RCM is one of the most efficient. 26 1. Vinyl (or allyl) lithium OTBDMS 2. Allylbromide COOMe O ( )n 3. 27 Mascare˜ nas et al. 27) [37]. Starting from 1,2cyclohexanedione, the dienes 166a and 166b were obtained. When submitted to RCM conditions ([Ru]-I, 20 ◦ C), only the diastereomers having the two unsaturated side chains in a syn relationship reacted.

As expected, RCM proved to be difficult and had to be performed under special conditions: the catalyst [Ru]-II (40 mol%) was slowly added, along with tetrafluoro-1,4-BQ (to prevent olefin isomerization), and the formed ethylene was removed during the reaction. Under these conditions, the RCM product 390 was obtained in a satisfactory yield (65%) and converted to ent-clavilactone B [103]. During the period 2001–2006, Gennari et al. published a series of accounts describing the synthesis, via RCM, of simplified eleuthesides as potential anticancer agents [104–106].

66 RCM strategy that was thwarted by conformational constraints imposing a cyclic carbonate protecting group of the C1–C2 diol motif. 6 Formation of Nine-membered Carbocycles by RCM The failed metathesis-based synthesis of pestalotiopsin A 359, compared to the successful synthesis of cornexistins, reported by Paquette et al. [96] and Clark et al. [97] illustrates well the uncertainty linked to RCM toward 8 to 10-membered rings. 2). For 360 and 361, regardless of the catalyst used ([Ru]-I, II, III, VII, and XI), the starting diene was either recovered (when the reaction was performed below 80 ◦ C) or decomposed (in refluxing toluene).

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Metathesis in Natural Product Synthesis: Strategies, Substrates and Catalysts by Janine Cossy, Stellios Arseniyadis, Christophe Meyer, Robert H. Grubbs


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