Jauch synthesis

Jauch achieved the short and elegant total synthesis of mniopetals during almost the same period in which our total syntheses were reported [36-41]. We briefly introduce Jauch s achievements on this subject. The key step of his synthesis was the IMDA reaction of 2-substituted butenolide 124 (Scheme 20), which was prepared by the diastereoselective PhSeLi-induced Baylis-Hillman reaction of 122 and Feringa s butenolide 123 [99]. The cycloadduct of this IMDA reaction 125 was transformed into kuehneromycin A and mniopetals E and F, respectively. 

Research by J. Jauch showed that in the case of highiy base-sensitive substrates the Baylis-Hillmann reaction can be carried out by using lithium phenylselenide, which is a strong nucieophile but oniy weakiy basic. This variant of the reaction is highly diastereoselective and was successfully applied to the total synthesis of kuehneromycin... 

Jauch, J. A short total synthesis of kuehneromycin A. Angew, Chem, Int, Ed, Engl, 2000, 39, 2764-2765. 

Jauch, J. Stereochemistry of the Rubottom oxidation with bicyclic silyl enol ethers synthesis and dimerization reactions of bicyclic a-hydroxy ketones. Tetrahedron 1994, 50,12903-12912. 

Jauch, J. (2001) A short synthesis of Mniopetal F. European Journal of Organic Chemistry, 413-416. 

Jauch, J., Synthetic studies towards mniopetals. Part 2. A short synthesis of mniopetal E, Synlett, 87,... 

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