Stereoselective synthesis of the C1-C20 segment of the microsclerodermins A and B

被引:11
作者
Chandrasekhar, S. [1 ]
Sultana, S. Shameem [1 ]
机构
[1] Indian Inst Chem Technol, Div Organ Chem, Hyderabad 500007, Andhra Pradesh, India
关键词
stereoselective; deoxygenative rearrangement; Iterative Sharpless asymmetric dihydroxylation; ANTIFUNGAL CYCLIC-PEPTIDES; ACID; ISOMERIZATION; AMINO;
D O I
10.1016/j.tetlet.2006.07.107
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An enantioselective route for the synthesis of key fragment Cl-C20 resident in microsclerodermins A and B is described. The route features deoxygenative rearrangement of an hydroxy-alkynoate and a highly enantio- and diastereo-controled iterative dihydroxylation as key reactions, starting from S-( - )-citronellol. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7255 / 7258
页数:4
相关论文
共 18 条
[1]   Amino analogs of actic acids -: synthesis and lactamization [J].
Bernsmann, H ;
Wang, YZ ;
Fröhlich, R ;
Metz, P .
TETRAHEDRON, 2002, 58 (22) :4451-4457
[2]   MICROSCLERODERMIN-A AND MICROSCLERODERMIN-B - ANTIFUNGAL CYCLIC-PEPTIDES FROM THE LITHISTID SPONGE MICROSCLERODERMA SP [J].
BEWLEY, CA ;
DEBITUS, C ;
FAULKNER, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (17) :7631-7636
[3]   The Sharpless asymmetric aminohydroxylation [J].
Bodkin, JA ;
McLeod, MD .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (24) :2733-2746
[4]   An expedient total synthesis of cis-(+)-Sertraline from D-phenylglycine [J].
Chandrasekhar, S ;
Reddy, MV .
TETRAHEDRON, 2000, 56 (08) :1111-1114
[5]  
FRIGERIO M, 1994, TETRAHEDRON LETT, V35, P8019, DOI 10.1016/S0040-4039(00)78412-7
[6]   Enantioselective synthesis of 10-epi-anamarine via an iterative dihydroxylation sequence [J].
Gao, D ;
O'Doherty, GA .
ORGANIC LETTERS, 2005, 7 (06) :1069-1072
[7]   A NOVEL DEOXYGENATION-ISOMERIZATION REACTION OF 4-HYDROXY-2-YNOIC ESTERS AND GAMMA-HYDROXY-ALPHA,BETA-YNONES [J].
GUO, C ;
LU, XY .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (04) :394-395
[8]   Catalytic asymmetric aminohydroxylation (AA) of olefins [J].
Li, GG ;
Chang, HT ;
Sharpless, KB .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (04) :451-454
[9]   Microsclerodermins F-I, antitumor and antifungal cyclic peptides from the lithistid sponge Microscleroderma sp. [J].
Qureshi, A ;
Colin, PL ;
Faulkner, DJ .
TETRAHEDRON, 2000, 56 (23) :3679-3685
[10]   Sulfinyl moiety as an internal nucleophile. Part 6: Stereospecific synthesis of 3-amino-2-hydroxy-4-phenylbutanoate [J].
Raghavan, S ;
Rasheed, MA .
TETRAHEDRON-ASYMMETRY, 2003, 14 (10) :1371-1374