By Taylor Stuart Ross, McLennan Scott M.
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Additional info for Solid earth geophysics 697-719 Chemical Composition and Element Distribution in the Earth's Crust
Sample text
Ether 467b formed with excellent diastereoselectivity (450:1), whereas ketone 467c was obtained as a 6:1-mixture of diastereomers. The disubstituted olefin 468 reacted in a similar fashion and gave 469 in 70% yield, though the diastereoselectivity (5:1) of the cyclization was significantly diminished. 5:1) diastereoselectivity. 2–6:1) diastereoselectivities. Using similar substituent placement to control relative rates, 7- and 8-membered rings were also constructed in 50–86% yields. K. BUR AND A.
The formation of tetracyclic 357 is interesting because this compound incorporates both the tetrahydropyrrolo[2,3-b]indole structure, which is found in physostigmine and related alkaloids, and the tetrahydroimidazo[1,2-a] indole skeleton, which is present in asperlicin and related natural products. V. 1,4-Additions A. MICHAEL ADDITION-INITIATED SEQUENCES Dihydropyridine derivatives can be formed from a cascade sequence wherein conjugate addition of enaminoesters occur with a,b-unsaturated carbonyl compounds Sec.
B. PUMMERER CASCADE REACTIONS The combination of a Pummerer-based reaction (04CR2401) followed by an N-acyliminium ion cyclization in tandem to form pyrrolidine-containing ring systems represents a unique method to synthesize heterocycles. In a typical example from the Padwa laboratory, enamide 299 was treated with p-TsOH in boiling benzene to produce thionium ion 300. A subsequent Nazarov-like ring closure of 300 furnished iminium ion 301. Finally, an intramolecular Pictet–Spengler reaction with the pendant aromatic ring of 301 provided 302 as a single diastereomer in 78% yield (Scheme 56) (98JOC6778, 02JOC5928).
Solid earth geophysics 697-719 Chemical Composition and Element Distribution in the Earth's Crust by Taylor Stuart Ross, McLennan Scott M.
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