Enantioselective synthesis of polyhydroxyindolizidinone and quinolizidinone derivatives from a common precursor

被引：3

作者：

Saha, Nemai ^{[1
]}

Chattopadhyay, Shital K. ^{[1
]}

机构：

[1] Univ Kalyani, Dept Chem, Kalyani 741235, W Bengal, India

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 10卷

关键词：

chiral pool; dihydroxylation; indolizidines; quinolizidine; ring-closing metathesis; GLYCOSIDASE INHIBITORS; POLYHYDROXYLATED INDOLIZIDINES; BIOLOGICAL-ACTIVITY; METATHESIS; (+)-LENTIGINOSINE; ACCESS; AGENTS;

D O I：

10.3762/bjoc.10.327

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise asymmetric synthetic route to two new tetrahydroxyindolizidinone and quinolizidinone derivatives has been developed from a common intermediate which featured a highly selective dihydroxylation reaction and a RCM reaction as key steps.

引用

页码：3104 / 3110

页数：7

共 38 条

[1] Glycosidase inhibitors: update and perspectives on practical use [J].

Asano, N .

GLYCOBIOLOGY, 2003, 13 (10) :93R-104R

[2] Sugar-mimic glycosidase inhibitors: natural occurrence, biological activity and prospects for therapeutic application [J].

Asano, N ;

Nash, RJ ;

Molyneux, RJ ;

Fleet, GWJ .

TETRAHEDRON-ASYMMETRY, 2000, 11 (08) :1645-1680

[3]

Asano Naoki, 2001, Mini-Reviews in Medicinal Chemistry, V1, P145, DOI 10.2174/1389557013407052

[4] A concise synthesis of lentiginosine derivatives using a pyridinium formation via the Mitsunobu reaction [J].

Azzouz, Rabah ;

Fruit, Corinne ;

Bischoff, Laurent ;

Marsais, Francis .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (03) :1154-1157

[5] Osmium-free direct syn-dihydroxylation of alkenes [J].

Bataille, Carole J. R. ;

Donohoe, Timothy J. .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (01) :114-128

[6] Synthesis and Glycosidase Inhibitory Study of New Polyhydroxylated Indolizidines [J].

Baumann, Delphine ;

Bennis, Khalil ;

Ripoche, Isabelle ;

Thery, Vincent ;

Troin, Yves .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (31) :5289-5300

[7] Conformational dynamics in nitrogen-fused azabicycles [J].

Belostotskii, AM ;

Markevich, E .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (08) :3055-3063

[8] α,β-Unsaturated Diazoketones as Platforms in the Asymmetric Synthesis of Hydroxylated Alkaloids. Total Synthesis of 1-Deoxy-8,8a-diepicastanospermine and 1,6-Dideoxyepicastanospermine and Formal Synthesis of Pumiliotoxin 251D [J].

Bernardim, Barbara ;

Pinho, Vagner D. ;

Burtoloso, Antonio C. B. .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (21) :9926-9931

[9] New concise total synthesis of (+)-lentiginosine and some structural analogues [J].

Cardona, F ;

Moreno, G ;

Guarna, F ;

Vogel, P ;

Schuetz, C ;

Merino, P ;

Goti, A .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (16) :6552-6555

[10] Total synthesis of (-)-lentiginosine [J].

Chandrasekhar, S. ;

Vijaykumar, B. V. D. ;

Pratap, T. V. .

TETRAHEDRON-ASYMMETRY, 2008, 19 (06) :746-750

← 1 2 3 4 →