Efficient synthesis of optically pure (4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(hydroxymethyl)tetrahydropyran-2-one and its enantiomer

被引:7
作者
Ghorpade, SR
Kalkote, UR [1 ]
Chavan, SP
Bhide, SR
Ravindranathan, T
Puranik, VG
机构
[1] Natl Chem Lab, Div Organ Chem, Pune 411008, Maharashtra, India
[2] Natl Chem Lab, Technol & Phys Chem Div, Pune 411008, Maharashtra, India
关键词
D O I
10.1021/jo015774s
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[No abstract available]
引用
收藏
页码:6803 / 6806
页数:4
相关论文
共 16 条
[1]   OXIDATION OF METHYL P-TOLYL SULFIDE WITH BAKERS-YEAST - PREPARATION OF A SYNTHON OF THE MEVINIC ACID-TYPE HYPOCHOLESTEMIC AGENTS [J].
BEECHER, J ;
BRACKENRIDGE, I ;
ROBERTS, SM ;
TANG, J ;
WILLETTS, AJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (13) :1641-1643
[2]  
BOCAN TMA, 1989, 10TH INT S DRUGS AFF, P55
[3]   CRYSTAL AND MOLECULAR-STRUCTURE OF COMPACTIN, A NEW ANTIFUNGAL METABOLITE FROM PENICILLIUM-BREVICOMPACTUM [J].
BROWN, AG ;
SMALE, TC ;
KING, TJ ;
HASENKAMP, R ;
THOMPSON, RH .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (11) :1165-1173
[4]   COMPETITIVE INHIBITION OF 3-HYDROXY-3-METHYLGLUTARYL COENZYME A REDUCTASE BY ML-236A AND ML-236B FUNGAL METABOLITES, HAVING HYPOCHOLESTEROLEMIC ACTIVITY [J].
ENDO, A ;
KURODA, M ;
TANZAWA, K .
FEBS LETTERS, 1976, 72 (02) :323-326
[5]   ML-236A, ML-236B, AND ML-236C, NEW INHIBITORS OF CHOLESTEROGENESIS PRODUCED BY PENICILLIUM CITRINUM [J].
ENDO, A ;
KURODA, M ;
TSUJITA, Y .
JOURNAL OF ANTIBIOTICS, 1976, 29 (12) :1346-1348
[6]   Desymmetrization of meso-cyclopenten-cis-1,4-diol to 4-(R)-hydroxycyclopent-2-en-1-(S)-acetate by irreversible transesterification using Chirazyme® [J].
Ghorpade, SR ;
Kharul, RK ;
Joshi, RR ;
Kalkote, UR ;
Ravindranathan, T .
TETRAHEDRON-ASYMMETRY, 1999, 10 (05) :891-899
[7]   Enzymatic kinetic resolution studies of racemic 4-hydroxycyclopent-2-en-1-one using Lipozyme IM® [J].
Ghorpade, SR ;
Bastawade, KB ;
Gokhale, DV ;
Shinde, PD ;
Mahajan, VA ;
Kalkote, UR ;
Ravindranathan, T .
TETRAHEDRON-ASYMMETRY, 1999, 10 (21) :4115-4122
[8]   TOTAL SYNTHESIS OF THE HYPOCHOLESTEROLEMIC AGENT COMPACTIN [J].
HSU, CT ;
WANG, NY ;
LATIMER, LH ;
SIH, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (03) :593-601
[9]   A practical and scalable process for 4-(R)-hydroxycyclopent-2-en-1-(S)-acetate by desymmetrization of meso-cyclopent-2-en-1,4-diacetate catalyzed by Trichosporon beigelii (NCIM 3326), a cheap biocatalyst [J].
Kalkote, UR ;
Ghorpade, SR ;
Joshi, RR ;
Ravindranathan, T ;
Bastawade, KB ;
Gokhale, DV .
TETRAHEDRON-ASYMMETRY, 2000, 11 (14) :2965-2970
[10]  
KATHAWALA F, 1988, Patent No. 4739073