Sequential Baylis-Hillman/RCM protocol for the stereoselective synthesis of (+)-MK7607 and (+)-streptol

被引:11
作者
Krishna, Palakodety Radha [1 ]
Kadiyala, Raghu Ram [1 ]
机构
[1] Indian Inst Chem Technol, Div Organ Chem 3, Discovery Lab, Hyderabad 500607, Andhra Pradesh, India
关键词
Cyclitols; Diastereoselective Baylis-Hillman reaction; Ring-closing metathesis; Hoveyda-Grubbs catalyst; Sharpless asymmetric epoxidation; (R; R)-Tartaric acid; CARBASUGARS; EFFICIENT;
D O I
10.1016/j.tetlet.2010.02.080
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Sequential Baylis-Hillman/ring-closing metathesis (RCM) approach toward the total synthesis of (+)-MK7607 and (+)-streptol starting from (R,R)-tartaric acid is reported. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2586 / 2588
页数:3
相关论文
共 19 条
[1]   Synthesis and conformational and biological aspects of carbasugars [J].
Arjona, Odon ;
Gomez, Ana M. ;
Cristobal Lopez, J. ;
Plumet, Joaquin .
CHEMICAL REVIEWS, 2007, 107 (05) :1919-2036
[2]   Efficient and recyclable monomeric and dendritic Ru-based metathesis catalysts [J].
Garber, SB ;
Kingsbury, JS ;
Gray, BL ;
Hoveyda, AH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (34) :8168-8179
[3]   Synthesis and metathesis reactions of a phosphine-free dihydroimidazole carbene ruthenium complex [J].
Gessler, S ;
Randl, S ;
Blechert, S .
TETRAHEDRON LETTERS, 2000, 41 (51) :9973-9976
[4]   A direct entry to carbasugars:: Asymmetric synthesis of 1-epi-(+)-MK7607 [J].
Grondal, Christoph ;
Enders, Dieter .
SYNLETT, 2006, (20) :3507-3509
[5]  
ISOGAI A, 1987, AGR BIOL CHEM TOKYO, V51, P2277
[6]   Diversity oriented synthesis of functionalized chiral tetrahydropyridines: Potential GABA receptor agonists and azasugars from natural amino acids via a sequential Baylis-Hillman reaction and RCM protocol [J].
Krishna, Palakodety Radha ;
Reddy, P. Srinivas .
JOURNAL OF COMBINATORIAL CHEMISTRY, 2008, 10 (03) :426-435
[7]   Diversely substituted sugar-linked α,β-unsaturated γ-lactones from sugar-derived Baylis-Hillman adducts via a RCM [J].
Krishna, Palakodety Radha ;
Narsingam, M. .
JOURNAL OF COMBINATORIAL CHEMISTRY, 2007, 9 (01) :62-69
[8]   Asymmetric Baylis-Hillman Reaction: An Enchanting Expedition [J].
Krishna, Palakodety Radha ;
Sachwani, Rachna ;
Reddy, Purumandla Srinivas .
SYNLETT, 2008, (19) :2897-2912
[9]   'Double asymmetric induction' as a novel tool for high stereocontrol in Baylis-Hillman reaction [J].
Krishna, PR ;
Sachwani, R ;
Kannan, V .
CHEMICAL COMMUNICATIONS, 2004, (22) :2580-2581
[10]   Use of a Baylis-Hillman adduct in the stereoselective synthesis of syributins via a RCM protocol [J].
Krishna, PR ;
Narsingam, M ;
Kannan, V .
TETRAHEDRON LETTERS, 2004, 45 (24) :4773-4775