[reaction: see text] N-Methoxy-N-methylamides (Weinreb amides) are converted efficiently into ketones by reaction with alkylidenetriphenylphosphoranes and in situ hydrolysis of the product.
Efficient Route to the Pineal Hormone Melatonin by Radical-Based Indole Synthesis. -Melatonine (VII) is synthesized in high overall yield. Mediation of the radical cyclization, cf. (III)→(IV), by (Me3Si)3SiH is more efficient than by N-ethylpiperidine hypophosphite. -(THOMSON, D. W.; COMMEUREUC, A. G. J.; BERLIN, S.; MURPHY*, J. A.; Synth. Commun. 33 (2003) 20, 3631-3641; Dep. Pure Appl. Chem., Univ. Strathclyde, Glasgow G1 1XL, UK; Eng.) -C. Oppel
[reaction: see text] Muscothiazoles A (2b) and B (2c) have been prepared by two approaches that differ in the order of assembly of the rings. Comparative studies show that substitution of the carbon chains in substrate 5 or 12 (respective precursors to 13-membered and 14-membered rings by RCM), even by a single methyl group, can have a profound effect on increasing the efficiency of the macrocyclization.
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