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In fact, under the same thermo condition, ortho-claisen rearrangement of 14 afforded diol 15 in 71 % yield (Scheme 3).
In the second method (Koenigs Knorr Method [11]) the mannoside (5) was obtained in 34 % overall yield (Scheme 3) [9].
Thus refluxing bromoketone 2 with aniline derivatives in EtOH for 6-8 h affording 9a-b in excellent yield (Scheme 3).
By Vilsmeier-Haack's reaction, starting from these sydnones we obtained the corresponding substituted 3-phenyl-4-formylsydnones in 17‒50 % yield (Scheme 1).
In 2013, our group reported the first total synthesis of -serinolamide A in nine steps from l-serine with 30% overall yield (Scheme 6) [50].
The three-step sequence [18] with assistance of microwave for the Vilsmeier–Haack formylation [19] proceeded well to afford 11 in 45 % yield (Scheme 4).
The procedure was carried out using in short reaction times, and the L-Boc-phenylalanilol 2 was isolated by simple filtration in high yield (Scheme 2).
Indeed, the condensation of isophthalonitrile with d-phenylglycinol (0.56 eq) afforded the predicted mono-chelated complex 9 [11] in a good yield (Scheme 4).
This compound was lithiated at −37 °C with n-BuLi and its subsequent reaction with Cp*TiCl3 afforded complex 57 in 45 % yield (Scheme 20, Fig. 16).
Treatment of the protected diamines 5 8 with (3:7 Et2NH/CH3CN v/v) easily furnished the required diamines 9 12, respectively, in high yield, Scheme 1.
By doubling the amount of base, 2a was isolated in 92% yield (Scheme 2).
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