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Oligomer-based approach to skeletal diversity employing metathesis cascades and Diels–Alder reactions as folding processes. Reagents and conditions: (1) Grubbs’ first-generation catalyst (5 mol%), benzene, ethylene, reflux, 12-24 h; 24a: d.r. >20 : 1, 57%; 24b: d.r. >15 : 1, 74%; 24c: d.r. >20 : 1, 56%; (2) 4-methyl-1,2,4-triazoline-3,5-dione, CH2Cl2, 0 °C to rt.; 25a: 93%; 25b: 90%; 25c: 46%. Ns = 2-nitrobenzenesulfonyl, Bs = 4-bromobenzenesulfonyl.
