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

[11]

Jansen R, 2000, EUR J ORG CHEM, V2000, P913, DOI 10.1002/(SICI)1099-0690(200003)2000:6<913::AID-EJOC913>3.0.CO

[12]

2-L

[13] Oximidines I and II:: Novel antitumor macrolides from Pseudomonas sp. [J].

Kim, JW ;

Shin-ya, K ;

Furihata, K ;

Hayakawa, Y ;

Seto, H .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (01) :153-155

[14] Enantioselective total synthesis of salicylihalamides A and B [J].

Labrecque, D ;

Charron, S ;

Rej, R ;

Blais, C ;

Lamothe, S .

TETRAHEDRON LETTERS, 2001, 42 (14) :2645-2648

[15] ONE POT PHASE-TRANSFER SYNTHESIS OF O-ALKYL, S-METHYL DITHIOCARBONATES (XANTHATES) [J].

LEE, AWM ;

CHAN, WH ;

WONG, HC ;

WONG, MS .

SYNTHETIC COMMUNICATIONS, 1989, 19 (3-4) :547-552

[16] SELECTIVE HYDRIDE-MEDIATED CONJUGATE REDUCTION OF ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS USING [(PH3P)CUH]6 [J].

MAHONEY, WS ;

BRESTENSKY, DM ;

STRYKER, JM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (01) :291-293

[17] The lobatamides, novel cytotoxic macrolides from southwestern Pacific tunicates [J].

McKee, TC ;

Galinis, DL ;

Pannell, LK ;

Cardellina, JH ;

Laakso, J ;

Ireland, CM ;

Murray, L ;

Capon, RJ ;

Boyd, MR .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (22) :7805-7810

[18] SYNTHESIS OF PARATOSE (3,6-DIDEOXY-D-RIBO-HEXOSE) [J].

PATRONI, JJ ;

STICK, RV .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1978, 31 (02) :445-446

[19] Total synthesis of (-)-salicylihalamide A and related congeners [J].

Smith, AB ;

Zheng, JY .

TETRAHEDRON, 2002, 58 (32) :6455-6471

[20]

Smith AB, 2001, SYNLETT, P1019

← 1 2 3 →