A total synthesis of (+)-negamycin through isoxazolidine allylation

被引：16

作者：

Bates, Roderick W. ^{[1
]}

Khanizeman, Rab'iah Nisha ^{[1
]}

Hirao, Hajime ^{[1
]}

Tay, Yu Shan ^{[1
]}

Sae-Lao, Patcharaporn ^{[1
]}

机构：

[1] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2014年 / 12卷 / 27期

关键词：

ENANTIOSELECTIVE TOTAL-SYNTHESIS; ASYMMETRIC-SYNTHESIS; NEGAMYCIN; ACID; N; O-HETEROCYCLES; SEDAMINE;

D O I：

10.1039/c4ob00537f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The beta-amino acid antibiotic (+)-negamycin has been synthesised in ten steps from epichlorohydrin via Sakurai allylation of an isoxazolidine intermediate. The key allylation reaction proceeded with complete trans-selectivity, which is attributed to electrostatic attraction between the chlorine atom and the iminium ion in the Sakurai intermediate.

引用

页码：4879 / 4884

页数：6

共 38 条

[1] Synthesis of N,O-heterocycles by intramolecular conjugate addition of a hydroxylamine [J].

Bates, Roderick W. ;

Snell, Robert H. ;

Winbush, SusAnn .

SYNLETT, 2008, (07) :1042-1044

[2] Synthesis of sedamine by cycloisomerisation of an allenic hydroxylamine [J].

Bates, Roderick W. ;

Nemeth, Joseph A. ;

Snell, Robert H. .

SYNTHESIS-STUTTGART, 2008, (07) :1033-1038

[3] N,O-Heterocycles as synthetic intermediates [J].

Bates, Roderick W. ;

Boonsombat, Jutatip ;

Lu, Yongna ;

Nemeth, Joseph A. ;

Sa-Ei, Kanicha ;

Song, Ping ;

Cai, Melody Peiling ;

Cranwell, Philippa B. ;

Winbush, SusAnn .

PURE AND APPLIED CHEMISTRY, 2008, 80 (04) :681-685

[4] A synthesis of 5-hydroxysedamine using hydroformylation [J].

Bates, Roderick W. ;

Aslam, Nur Filza Bte Mohamed ;

Tang, Chi H. ;

Simon, Oliver .

TETRAHEDRON, 2014, 70 (12) :2134-2140

[5] Allylation Reactions of N,O-Heterocycles [J].

Bates, Roderick W. ;

Tang, Chi H. ;

Tan, Yuting ;

Buang, Siti Nurhayati Binte .

SYNLETT, 2012, (15) :2266-2268

[6] Synthesis of (-)-Sedinine by Allene Cyclization and Iminium Ion Chemistry [J].

Bates, Roderick W. ;

Lu, Yongna .

ORGANIC LETTERS, 2010, 12 (17) :3938-3941

[7] Synthesis of Two Nuphar Alkaloids by Allenic Hydroxylamine Cyclisation [J].

Bates, Roderick W. ;

Lim, Chia Juan .

SYNLETT, 2010, (06) :866-868

[8] A Formal Synthesis of Porantheridine and an Epimer [J].

Bates, Roderick W. ;

Lu, Yongna .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (24) :9460-9465

[9] Synthesis of sedamine by tethered cyclofunctionalisation [J].

Bates, RW ;

Boonsombat, J .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (03) :520-523

[10] O-alkenyl hydroxylamines:: A new concept for cyclofunctionalization [J].

Bates, RW ;

Sa-Ei, K .

ORGANIC LETTERS, 2002, 4 (24) :4225-4227

← 1 2 3 4 →