Enantiospecific formal total syntheses of (-)-salicylihalamides A and B from D-Glucose and L-rhamnose

被引:14
|
作者
Yang, KL
Haack, T
Blackman, B
Diederich, WE
Roy, S
Pusuluri, S
Georg, GI
机构
[1] Univ Kansas, Ctr Canc Expt Therapeut, Dept Med Chem, Lawrence, KS 66045 USA
[2] Univ Kansas, Higuchi Biosci Ctr, Drug Discovery Program, Lawrence, KS 66045 USA
关键词
D O I
10.1021/ol035630v
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Two formal chiral pool syntheses of the (-)-salicylihalamides A and B were achieved from commercially available 1,2,5,6-diacetone-D-glucose and L-rhamnose.
引用
收藏
页码:4007 / 4009
页数:3
相关论文
共 50 条
  • [21] Total synthesis of pachastrissamine (jaspine B) enantiomers from D-glucose
    Ramana, C. V.
    Giri, Awadut G.
    Suryawanshi, Sharad B.
    Gonnade, Rajesh G.
    TETRAHEDRON LETTERS, 2007, 48 (02) : 265 - 268
  • [22] Formal Synthesis of Salinosporamide A Starting from D-Glucose
    Momose, Takayuki
    Kaiya, Yuji
    Hasegawa, Jun-ichi
    Sato, Takaaki
    Chida, Noritaka
    SYNTHESIS-STUTTGART, 2009, (17): : 2983 - 2991
  • [23] STANNYLENE MEDIATED CHEMOSELECTIVITY .10. ALTERNATIVE SYNTHESES OF L-(-)-OLEANDROSE FROM L-RHAMNOSE PREPARATION OF GLYCALS
    BREDENKAMP, MW
    HOLZAPFEL, CW
    TOERIEN, F
    SYNTHETIC COMMUNICATIONS, 1992, 22 (17) : 2459 - 2477
  • [24] Total synthesis of (+)-lentiginosine from D-glucose
    Alam, Mohammad Abrar
    Vankar, Yashwant D.
    TETRAHEDRON LETTERS, 2008, 49 (38) : 5534 - 5536
  • [25] TOTAL SYNTHESIS OF (+)-SESBANIMIDE A FROM D-GLUCOSE
    TOMIOKA, K
    HAGIWARA, A
    KOGA, K
    TETRAHEDRON LETTERS, 1988, 29 (25) : 3095 - 3096
  • [26] TOTAL SYNTHESIS OF (+)-LACTACYSTIN FROM D-GLUCOSE
    CHIDA, N
    TAKEOKA, J
    TSUTSUMI, N
    OGAWA, S
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (07) : 793 - 794
  • [27] Total synthesis of paniculide A from D-glucose
    Amano, S
    Takemura, N
    Ohtsuka, M
    Ogawa, S
    Chida, N
    TETRAHEDRON, 1999, 55 (13) : 3855 - 3870
  • [28] Production of L-rhamnulose, a rare sugar, from L-rhamnose using commercial immobilized glucose isomerase
    Kim, Yeong-Su
    Kim, Do-Yeon
    Park, Chang-Su
    BIOCATALYSIS AND BIOTRANSFORMATION, 2018, 36 (06) : 417 - 421
  • [29] ENANTIOSPECIFIC SYNTHESIS OF (R)-(+)-ALPHA-LIPOIC ACID FROM D-GLUCOSE
    RAO, AVR
    GURJAR, MK
    GARYALI, K
    RAVINDRANATHAN, T
    CARBOHYDRATE RESEARCH, 1986, 148 (01) : 51 - 55
  • [30] Enantiospecific synthesis of 8-O-methylthioswainsonine from a derivative of D-glucose
    Izquierdo, I
    Plaza, MT
    Aragon, F
    TETRAHEDRON-ASYMMETRY, 1996, 7 (09) : 2567 - 2575