Download Metathesis in natural product synthesis : strategies, by Janine Cossy, Stellios Arseniyadis, Christophe Meyer, Robert PDF

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

Emphasizing the effect of metathesis in common product synthesis during the sorts of key reactions, this prepared reference is obviously dependent and filled with vital details, together with consultant experimental systems for functional applications.

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Extra resources for Metathesis in natural product synthesis : strategies, substrates and catalysts

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As shown by MM3 calculations on model systems, the closer proximity of these two substituents in the 2,3 isomer could allow a more RCM. 65). Prunet et al. 66) [95]. 66). 66). Unprotected diol 357 led to the desired cyclooctene ring 358 in an impressive quantitative yield, thus suggesting that the BC ring system of taxol may be synthesized according to this strategy. 66 RCM strategy that was thwarted by conformational constraints imposing a cyclic carbonate protecting group of the C1–C2 diol motif.

Two simultaneous RCM have been used in efforts toward the core structure of the elisabethin diterpenoids [18]. 15). Tetrasubstituted double bonds embedded in a five-membered ring can also be efficiently prepared via RCM. 15 OAc [Ru]-II HO (5 mol%) TBSO OH 103 AcO Steps OTBS N2 104 Steps H O O O Bu3SnH AIBN H Toluene H O O O O 107 106 O 105 MeS(S)CO H Cu(II) cat O C6H6 reflux 82% O 108 HO HO I 1. KOH MeOH 2. HCl 3. 16 O O Spirotenuipesine B (102) HO Spirotenuipesine A (101) 9 1 Synthesis of Natural Products Containing Medium-size Carbocycles 10 and B (102), Danishefsky et al.

2 Formation of Five-membered Carbocycles by RCM O R*O Steps R*O SnCl4, −78 °C O [Ru]-II (5 mol%) OH O 72 O 73 (dr = 10 : 1) R = (1S,2R )-2-Phenylcyclohexyl OBn Toluene, reflux 86% OBn O 74 75 Cu(CN)(2-Th)Li2 PO O 76: P = TBDPS 1. KHMDS 2. TBSOTf 11 PO BF3·OEt2 THF, −40 °C OBn O O PO 3. 4 : 1) O Steps THF O PMBO OH O O SEt 1. IBX, DMSO 2. 12 community. Paquette et al. reported a straightforward strategy for the elaboration of both antipodes of fomannosin. Compound 80 (prepared from α-d-glucose) underwent a zirconium-promoted ring contraction providing the four-membered ring 81.

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