173935-16-5Relevant academic research and scientific papers
Syntheses of optically pure conduramines via the strategy of hetero diels-alder reaction of masked o -benzoquinones with homochiral nitroso dienophiles
Lu, Ping-Hsun,Yang, Ching-Shun,Devendar, Badugu,Liao, Chun-Chen
supporting information; experimental part, p. 2642 - 2645 (2010/08/22)
Highly stereoselective hetero Diels-Alder reactions of masked o-benzoquinones (MOBs) with homochiral nitroso dienophiles are described along with their application in the syntheses of (+)-ent-conduramine F-1, (+)-conduramine E-1, (-)-conduramine A-1, (+)-
A flexible strategy based on a C2-symmetric pool of chiral substrates: Concise synthesis of (+)-valienamine, key intermediate of (+)- pancratistatin, and conduramines A-1 and E
Chang, Yuan-Kang,Lo, Hong-Jay,Yan, Tu-Hsin
supporting information; experimental part, p. 4278 - 4281 (2010/01/16)
A new strategy invoking a new application of the [3,3] sigmatropic rearrangement of allylic azides and the presence of a C2 symmetry element within a pool of chiral substrates was evolved. Not only does this simple flexible strategy provide a concise approach to (+)-valienamine, but it also can readily be adopted for the synthesis of conduramines A-1 and E and the enantiopure azido carbonate 4, a key intermediate of (+)-pancratistatin.
Desymmetrisation of dienylsilanes. Stereoselective access to cyclitols and carba-sugars
Landais, Yannick
, p. 104 - 111 (2007/10/03)
The diastereo- and enantioselective functionalisation of 1,4-cyclohexadienylsilanes using Sharpless asymmetric dihydroxylation and aminohydroxylation offers a straightforward access to various classes of potent inhibitors of glycosidases. The scope and limitation of this desymmetrisation method is illustrated here with the synthesis of various conduritols, carba-sugars and carba-C-disaccharides.
Total synthesis of acanthacerebroside A and astrocerebroside A via a chiral epoxide intermediate derived from L-quebrachitol
Chida, Noritaka,Sakata, Noboru,Murai, Katsuyuki,Tobe, Takahiko,Nagase, Toshihiko,Ogawa, Seiichiro
, p. 259 - 272 (2007/10/03)
The chiral and stereoselective total synthesis of novel cerebrosides, acanthacerebroside A (1) and astrocerebroside A (2), isolated from starfish, is described. The phytosphingosine moieties in 1 and 2 were prepared by the coupling reaction of dialkylmagnesium reagents with the common epoxide intermediate, 2-(t-butoxycarbonyl)amino-1-O-(t-butyldiphenylsilyl)-2-deoxy- 3-O-(4-methoxybenzyl)-D-4,5-anhydroribitol (5). The epoxide (5) was synthesized from naturally occurring cyclitol, L-quebrachitol via the conduramine derivative, which was prepared regio- and stereoselectively by the Pd-catalyzed azidation of the allyl carbonate derivative. Condensation of phytosphingosines with 2-acetoxy fatty acid residue, followed by glycosidation, furnished the total synthesis. This work established an effective synthetic pathway to a wide variety of cerebrosides containing various phytosphingosines and 2-hydroxy fatty acid residue; the first total synthesis of astrocerebroside A (2) fully confirmed the proposed structure.
On the flexibility of allylic azides as synthetic intermediates
Trost,Trost, Barry M.,Pulley,Pulley, Shon R.
, p. 8737 - 8740 (2007/10/02)
Asymmetric synthesis of an allylic azide combined with the facility of the [3.3]sigmatropic rearrangement provides a simple strategy for the synthesis of conduramine E.
