Total Synthesis of Mallotusinin.
Total Synthesis of Mallotusinin.
复制标题
Mallotusinin 的全合成。
作者：
K. Yamashita;Yuji Kume;Seiya Ashibe;Cicilia A D Puspita;Kotaro Tanigawa;Naoki Michihata;Shinnosuke Wakamori;Kazutada Ikeuchi;H. Yamada
本文报道了以3，6-O-(R)-六羟基联苯甲酰(HHDP)桥连接葡萄糖的2-氧和4-氧之间的四羟基二苯并呋喃(THDBF)桥的马洛菌素的全合成。全合成的主要特点是：(1)改进了我们以前报道的合成Corilagin的方法；(2)通过HHDP类似物的不寻常的分子内S N-Ar反应形成了THDBF骨架；(3)将HHDP桥的两步双离化法应用到2，4-O-THDBF桥的建设中。1，2，4-邻乙酰基-3，6-二-(4-O-苯基没食子酰基)-α-D-吡喃葡萄糖的苯酚氧化偶联和偶联产物的邻酯裂解而不发生吡喃糖-呋喃糖环转化是改进柯里拉金合成的关键反应，为马洛菌素的合成提供了充足的前驱体。这些已建立的方法有望开发出在柯里拉金的两个氧基之间架起桥梁的其他鞣胶的合成方法。
We describe the total synthesis of mallotusinin that bears a tetrahydroxydibenzofuranoyl (THDBF) bridge between the 2-oxygen and 4-oxygen of glucose on corilagin with a 3,6- O -( R )-hexahydroxydiphenoyl (HHDP) bridge. The key features of the total synthesis are: (1) improvements of our previously reported method to synthesize corilagin; (2) an establishment of forming the THDBF skeleton via an unusual intramolecular S N Ar reaction of an HHDP analog, and (3) the application of two-step bislactonization strategy for an HHDP bridge construction into the 2,4- O -THDBF bridge construction. Oxidative phenol coupling of 1,2,4-orthoacetyl-3,6-di-(4- O -benzylgalloyl)-α-D-glucopyranose and the orthoester cleavage of the coupling product without the pyranose-furanose ring transformation are key reactions for the improvement synthesis of corilagin, which enabled the adequate supplement of a corilagin precursor for developing the mallotusinin synthesis. These established methods are expected to development of the synthesis of other ellagitannins with a bridge between the two oxygens of corilagin.
影响因子：
2.7
作者：
Teng, Heidi;Thakur, Ganesh A.;Makriyannis, Alexandros
通讯作者：
Makriyannis, Alexandros
对映体纯 5,13-二氰基-9-氧杂[7]螺旋烯：合成和研究。
影响因子：
2.8
作者：
Gupta,Riddhi;Cabreros,TrevorA;Muller,Gilles;Bedekar,AshutoshV
通讯作者：
Bedekar,AshutoshV