Enantiospecific formal total syntheses of (-)-salicylihalamides A and B from D-Glucose and L-rhamnose

被引：14

作者：

Yang, KL

Haack, T

Blackman, B

Diederich, WE

Roy, S

Pusuluri, S

Georg, GI

机构：

[1] Univ Kansas, Ctr Canc Expt Therapeut, Dept Med Chem, Lawrence, KS 66045 USA

[2] Univ Kansas, Higuchi Biosci Ctr, Drug Discovery Program, Lawrence, KS 66045 USA

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 21期

关键词：

D O I：

10.1021/ol035630v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two formal chiral pool syntheses of the (-)-salicylihalamides A and B were achieved from commercially available 1,2,5,6-diacetone-D-glucose and L-rhamnose.

引用

页码：4007 / 4009

页数：3

共 27 条

[1] Synthesis of the core structure of salicylihalamide A by intramolecular Suzuki reaction [J].

Bauer, M ;

Maier, ME .

ORGANIC LETTERS, 2002, 4 (13) :2205-2208

[2] PREPARATION OF 2-DEOXY, 3-DEOXY, AND 4-DEOXY DERIVATIVES OF L-RHAMNOSE, AND DERIVATIVES OF 2-AZIDO-2-DEOXY-L-RHAMNOSE AND 2,6-DIDEOXY-2-FLUORO-L-GLUCOSE, FOR USE IN GLYCOSYLATION REACTIONS [J].

BOLS, M ;

LUNDT, I ;

OTTOSEN, ER .

CARBOHYDRATE RESEARCH, 1991, 222 :141-149

[3]

Boyd MR, 2001, J PHARMACOL EXP THER, V297, P114

[4] Salicylihalamides A and B, novel cytotoxic macrolides from the marine sponge Haliclona sp. [J].

Erickson, KL ;

Beutler, JA ;

Cardellina, JH ;

Boyd, MR .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (23) :8188-8192

[5]

Fürstner A, 2001, CHEM-EUR J, V7, P5286, DOI 10.1002/1521-3765(20011217)7:24<5286::AID-CHEM5286>3.0.CO

[6]

2-G

[7] Asymmetric synthesis of the fully functional macrolide core of salicylihalamide:: Remote control of olefin geometry during RCM [J].

Fürstner, A ;

Thiel, OR ;

Blanda, G .

ORGANIC LETTERS, 2000, 2 (23) :3731-3734

[8] Short and efficient chiral pool and RCM approach towards the synthesis of the macrocyclic core of the salicylihalamides [J].

Georg, GI ;

Ahn, YM ;

Blackman, B ;

Farokhi, F ;

Flaherty, PT ;

Mossman, CJ ;

Roy, S ;

Yang, KL .

CHEMICAL COMMUNICATIONS, 2001, (03) :255-256

[9] Formal total synthesis of salicylihalamides A and B [J].

Holloway, GA ;

Hügel, HM ;

Rizzacasa, MA .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (06) :2200-2204

[10]

IACONO S, 1990, ORG SYNTH, V7, P139

← 1 2 3 →