Ethylenediamine (H2NCH2CHeNH2) was found to be a highly effective catalyst for the condensation of aryl aldehydes with nitromethane (or nitroethane). When 1%-2% (tool%) of ethylenediamine was used as the catalyst, the one-pot reaction of aryl aldehydes with nitromethane (or nitroethane) by refluxing for 3-10 h efficiently afforded various arylnitroalkenes la-ly in 85%-97% yields.
Yang Jianxin Dong Jing Lu Xia Zhang Qiang Ding Wei Shi Xiaoxin
A novel total synthesis of Mansouramycin B (1) was performed via 10 steps in 28% overall yield starting from the readily available and cheap salicylaldehyde. Two key steps of this total synthesis are noteworthy. The first one is base-promoted one-pot aerobic aromatization of N-tosyltetrahydroisoquinoline 6, the second one is oxidation of 5-hydroxy-3-methyl-isoquinoline 8 with iodobenzene diacetate [PhI(OAc)2].
A base-catalyzed ring-opening of 1-benzylisochromans 1 firstly produced 2-alkenylstilbenes 2, which then underwent a mild acid-catalyzed intramolecular cyclization to furnish 1,2-disubstituted indenes 3 in high yields. Subsequently, a base-catalyzed isomerization of the 1,2-disubstituted indenes 3 afforded the more stable 2,3-disubstituted indenes 4 in almost quantitative yields.
All of the four stereoisomers of methyl 4,5-epoxy-3-hydroxy-cyclohex-l-ene-carboxylate (la--ld) are useful chiral building blocks. Novel and efficient syntheses of these four epoxy chiral building blocks from naturally abun- dant (--)-shikimic acid (2) via cyclic sulfite intermediates are described in this article. The targeted compound (3R,4R,5S)-la was synthesized via four steps from (--)-shikimic acid in 79% overall yield. The other three targeted compounds (3S,4R,5S)-lb, (3S,4S,5R)-1c and (3R,4S,5R)-ld were synthesized via seven steps from (--)-shikimic acid in 56%, 64% and 65% overall yields, respectively.
Quan Na Nie Liangdeng Shi Xiaoxin Zhu Ruiheng Lu Xian