Total synthesis of 3-epi-(+)-lycoricidine from Gamer aldehyde via intramolecular aldol cyclization

被引：8
作者：
Bera, Saurav
Das, Sanjit Kumar
Saha, Hash
Panda, Gautam [1 ]
机构：
[1] CSIR, Cent Drug Res Inst, Med & Proc Chem Div, Lucknow 226031, Uttar Pradesh, India
来源：
TETRAHEDRON LETTERS | 2015年 / 56卷 / 01期
关键词：
Lycoricidine; Garner aldehyde; Aldol cyclization; ENANTIOSPECIFIC SYNTHESIS; AMARYLLIDACEAE ALKALOIDS; NARCICLASINE ALKALOIDS; ANTINEOPLASTIC AGENTS; CHEMICAL-CONSTITUENTS; BIOLOGICAL EVALUATION; SHORT ROUTE; PANCRATISTATIN; LYCORICIDINE; ANALOGS;
D O I：
10.1016/j.tetlet.2014.11.045
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A highly efficient total synthesis of 3-epi-(+)-lycoricidine has been described for the first time from easily available (S)-Garner aldehyde with an overall yield of 7% in 20 steps. Stereoselective nucleophilic addition, Sharpless asymmetric dihydroxylation, Dess-Martin periodinane oxidation, intramolecular aldol cyclization, and Luche reduction are the salient features of this approach. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码：146 / 149
页数：4
相关论文
共 58 条
[1]   BINDING OF (H-3)NARCICLASINE TO EUKARYOTIC RIBOSOMES - STUDY ON A STRUCTURE-ACTIVITY RELATIONSHIP [J].
BAEZ, A ;
VAZQUEZ, D .
BIOCHIMICA ET BIOPHYSICA ACTA, 1978, 518 (01) :95-103
[2]   NARCICLASINE - ANTITUMOR ALKALOID WHICH BLOCKS PEPTIDE-BOND FORMATION BY EUKARYOTIC RIBOSOMES [J].
CARRASCO, L ;
FRESNO, M ;
VAZQUEZ, D .
FEBS LETTERS, 1975, 52 (02) :236-239
[3]   STEREOSELECTIVE TOTAL SYNTHESIS OF (+)-LYCORICIDINE [J].
CHIDA, N ;
OHTSUKA, M ;
OGAWA, S .
TETRAHEDRON LETTERS, 1991, 32 (35) :4525-4528
[4]   TOTAL SYNTHESIS OF (+)-LYCORICIDINE AND ITS 2-EPIMER FROM D-GLUCOSE [J].
CHIDA, N ;
OHTSUKA, M ;
OGAWA, S .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (16) :4441-4447
[5]   ENANTIOSPECIFIC SYNTHESIS AND BIOLOGICAL EVALUATION OF SECO ANALOGS OF ANTITUMOR AMARYLLIDACEAE ALKALOIDS [J].
CHRETIEN, F ;
AHMED, SI ;
MASION, A ;
CHAPLEUR, Y .
TETRAHEDRON, 1993, 49 (34) :7463-7478
[6]   Formal Total Synthesis of (-)-Raphidecursinol B [J].
Das, Sanjit Kumar ;
Das, Sajal Kumar ;
Panda, Gautam .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (26) :5100-5107
[7]   A new route to 1,4-oxazepanes and 1,4-diazepanes from Garner aldehyde [J].
Das, Sanjit Kumar ;
Srivastava, Ajay Kumar ;
Panda, Gautam .
TETRAHEDRON LETTERS, 2010, 51 (11) :1483-1485
[8]   Asymmetric total syntheses of spisulosine, its diastereo- and regio-isomers [J].
Dinda, Subal Kumar ;
Das, Sajal Kumar ;
Panda, Gautam .
TETRAHEDRON, 2010, 66 (47) :9304-9309
[9]   A short synthesis of (+)-narciclasine via a strategy derived from stereocontrolled epoxide formation and SnCl4-catalyzed arene-epoxide coupling [J].
Elango, S ;
Yan, TH .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (20) :6954-6959
[10]   FURTHER EXPERIMENTS ON STRUCTURE-ACTIVITY-RELATIONSHIPS AMONG THE LYCORINE ALKALOIDS [J].
EVIDENTE, A ;
ARRIGONI, O ;
LISO, R ;
CALABRESE, G ;
RANDAZZO, G .
PHYTOCHEMISTRY, 1986, 25 (12) :2739-2743
123456