An expeditious stereoselective synthesis of natural (-)-Cassine via cascade HWE [3+2]-cycloaddition process

被引:23
作者
Herdeis, C [1 ]
Küpper, P [1 ]
Plé, S [1 ]
机构
[1] Univ Wurzburg, Inst Pharm & Lebensmittelchem, D-97074 Wurzburg, Germany
关键词
D O I
10.1039/b516888k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
L-Rhamnose is transformed to (-)-Cassine via a remarkable four step one pot reaction. The Horner-Wadsworth-Emmons [3 + 2]-1,3-dipolar cycloaddition reaction cascade is the pivotal step in this reaction sequence and makes the synthesis highly efficient.
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页码:524 / 529
页数:6
相关论文
共 59 条
[1]   Synthesis of 1-deoxy-D-galactohomonojirimycin via enantiomerically pure allenylstannanes [J].
Achmatowicz, M ;
Hegedus, LS .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (07) :2229-2234
[2]   Stereodivergent synthesis of enantiopure cis- and trans-3-ethyl-4-piperidineacetates [J].
Amat, M ;
Pérez, M ;
Llor, N ;
Bosch, J .
ORGANIC LETTERS, 2002, 4 (16) :2787-2790
[3]   Conjugate addition of organocuprates to chiral bicyclic δ-lactams.: Enantioselective synthesis of cis-3,4-disubstituted and 3,4,5-trisubstituted piperidines [J].
Amat, M ;
Pérez, M ;
Llor, N ;
Bosch, J ;
Lago, E ;
Molins, E .
ORGANIC LETTERS, 2001, 3 (04) :611-614
[4]   Asymmetric synthesis of fagomine and its congeners [J].
Banba, Y ;
Abe, C ;
Nemoto, H ;
Kato, A ;
Adachi, I ;
Takahata, H .
TETRAHEDRON-ASYMMETRY, 2001, 12 (06) :817-819
[5]   PERESTERS .5. DI-TERT-BUTYLPEROXYOXALATE [J].
BARTLETT, PD ;
BENZING, EP ;
PINCOCK, RE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (07) :1762-1768
[6]   REACTIONS OF RELEVANCE TO CHEMISTRY OF AMINOGLYCOSIDE ANTIBIOTICS .7. CONVERSION OF THIOCARBONATES INTO DEOXY-SUGARS [J].
BARTON, DHR ;
SUBRAMANIAN, R .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (15) :1718-1723
[7]   NEW METHOD FOR DEOXYGENATION OF SECONDARY ALCOHOLS [J].
BARTON, DHR ;
MCCOMBIE, SW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (16) :1574-1585
[8]   HORNER-WADSWORTH-EMMONS REACTION - USE OF LITHIUM-CHLORIDE AND AN AMINE FOR BASE SENSITIVE COMPOUNDS [J].
BLANCHETTE, MA ;
CHOY, W ;
DAVIS, JT ;
ESSENFELD, AP ;
MASAMUNE, S ;
ROUSH, WR ;
SAKAI, T .
TETRAHEDRON LETTERS, 1984, 25 (21) :2183-2186
[9]   1-aza sugars, apparent transition state analogues of equatorial glycoside formation/cleavage [J].
Bols, M .
ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (01) :1-8
[10]  
BROWN E, 1975, TETRAHEDRON LETT, P2881