(E)-2-((4R, 5R)-5-((Benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-ene-1,4-diol

被引:1
作者
Carreras, Carlos R. [1 ]
Garcia, Celina E. [2 ]
Martin, Victor S. [2 ]
Tonn, Carlos E. [1 ]
Diaz Diaz, David [3 ,4 ]
Pedro Cenal, Juan [1 ]
机构
[1] Univ Nacl San Luis, Fac Quim Bioquim & Farm, INTEQUI CONICET, San Luis, Argentina
[2] Univ La Laguna, Inst Univ Bioorgan Antonio Gonzalez, Tenerife 38206, Spain
[3] Univ Regensburg, Inst Organ Chem, D-93040 Regensburg, Germany
[4] Univ Zaragoza, CSIC, ICMA, E-50009 Zaragoza, Spain
关键词
reduction; DIBAL-H; substituted butenolides; allylic diols;
D O I
10.3390/M676
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of (E)-2-((4R,5R)-5-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-ene-1,4-diol by a one-step reduction of the appropriate 2-substituted butenolide is reported. Product characterization was carried out by IR, H-1 NMR, C-13 NMR, MS, elemental analysis and optical rotation.
引用
收藏
页数:4
相关论文
共 21 条
[1]   Gold-Catalyzed Dehydrative Cyclization of Allylic Diols [J].
Aponick, Aaron ;
Biannic, Berenger .
SYNTHESIS-STUTTGART, 2008, (20) :3356-3359
[2]  
Armarego W. L. F., 1996, PURIFICATION LAB CHE
[3]   Acid-mediated highly regioselective oxidation of substituted furans:: A simple and direct entry to substituted butenolides [J].
Ceñal, JP ;
Carreras, CR ;
Tonn, CE ;
Padrón, JI ;
Ramírez, MA ;
Díaz, DD ;
García-Tellado, F ;
Martín, VS .
SYNLETT, 2005, (10) :1575-1578
[4]   An improved synthesis of (2E,4Z)-6-(benzyloxy)-4-bromohexa-2,4-dien-1-ol [J].
Clarke, Paul A. ;
Rolla, Gabriele A. ;
Cridland, Andrew P. ;
Gill, Andrew A. .
TETRAHEDRON, 2007, 63 (37) :9124-9128
[5]   Total synthesis of terpenoids isolated from Caulerpale algae and their inhibition of tubulin assembly [J].
Commeiras, L ;
Bourdron, J ;
Douillard, S ;
Barbier, P ;
Vanthuyne, N ;
Peyrot, V ;
Parrain, JL .
SYNTHESIS-STUTTGART, 2006, (01) :166-181
[6]   Concise enantioselective synthesis of furocaulerpin [J].
Commeiras, L ;
Parrain, JL .
TETRAHEDRON-ASYMMETRY, 2004, 15 (03) :509-517
[7]   On the construction of 2-substituted 1,4-diacetoxybutadiene moiety:: application to the synthesis of (±)-caulerpenyne [J].
Commeiras, L ;
Santelli, M ;
Parrain, JL .
TETRAHEDRON LETTERS, 2003, 44 (11) :2311-2314
[8]   Efficient synthesis of (±)-dihydrorhipocephalin, a bioactive terpenoid from Caribbean marine algae of the Genera Penicillus and Udotea [J].
Commeiras, L ;
Valls, R ;
Santelli, M ;
Parrain, JL .
SYNLETT, 2003, (11) :1719-1721
[9]  
Commeiras L, 2002, SYNLETT, P743
[10]   First total synthesis of (±)-taxifolial A and (±)-iso-caulerpenyne [J].
Commeiras, L ;
Santelli, M ;
Parrain, JL .
ORGANIC LETTERS, 2001, 3 (11) :1713-1715