Asymmetric synthesis of the core of AMPTD, the key amino acid of microsclerodermins F-I

被引：13

作者：

Burnett, Cameron M.

Williams, Robert M. ^{[1
]}

机构：

[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 39期

基金：

美国国家卫生研究院;

关键词：

ALDOL ADDITIONS; STEREOSELECTIVE-SYNTHESIS; AMMTD;

D O I：

10.1016/j.tetlet.2009.06.144

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report a stereoselective synthesis of the five consecutive stereocenters of AMPTD in seven steps. Highlights include an Evans glycolate aldol reaction, the use of a Weinreb amide as an aldehyde masking group, and a Mannich reaction with an Ellman-type chiral sulfimine. (C) 2009 Elsevier Ltd. All rights reserved.

引用

收藏

页码：5449 / 5451

页数：3

相关论文

共 11 条

[1] Highly selective syn glycolate aldol reactions with boron enolates of Masamune norephedrine esters [J].

Andrus, MB ;

Sekhar, BBVS ;

Turner, TM ;

Meredith, EL .

TETRAHEDRON LETTERS, 2001, 42 (41) :7197-7201

[2] Anti-selective glycolate aldol additions with an oxapyrone boron enolate [J].

Andrus, MB ;

Sekhar, BBVS ;

Meredith, EL ;

Dalley, NK .

ORGANIC LETTERS, 2000, 2 (19) :3035-3037

[3] SYNTHESIS OF FLUORESCENT-PROBES FOR LOCALIZED MEMBRANE FLUIDITY MEASUREMENTS [J].

BECK, A ;

HEISSLER, D ;

DUPORTAIL, G .

TETRAHEDRON, 1991, 47 (08) :1459-1472

[4]

Crimmins MT, 2004, SYNLETT, P1371

[5] Asymmetric induction in methyl ketone aldol additions to α-alkoxy and α,β-bisalkoxy aldehydes:: A model for acyclic stereocontrol [J].

Evans, David A. ;

Cee, Victor J. ;

Siska, Sarah J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (29) :9433-9441

[6]

Hennings DD, 2000, SYNTHESIS-STUTTGART, P1310

[7] Rapid assembly of the polyhydroxylated β-amino acid constituents of microsclerodermins C, D, and E [J].

Hjelmgaard, Thomas ;

Faure, Sophie ;

Lemoine, Pascale ;

Viossat, Bernard ;

Aitken, David J. .

ORGANIC LETTERS, 2008, 10 (05) :841-844

[8]

ONISHI T, 2007, Patent No. 7173141

[9] Microsclerodermins F-I, antitumor and antifungal cyclic peptides from the lithistid sponge Microscleroderma sp. [J].

Qureshi, A ;

Colin, PL ;

Faulkner, DJ .

TETRAHEDRON, 2000, 56 (23) :3679-3685

[10] The efficient stereoselective synthesis of (2S,3R,4S,5S,6S,11E)-3-amino-6-methyl-12-(4-methoxyphenyl)-2,4,5-trihydroxydodec-11-enoic acid (AMMTD), a component of microsclerodermins of marine sponge origin, as its protected form [J].

Sasaki, S ;

Hamada, Y ;

Shioiri, T .

TETRAHEDRON LETTERS, 1999, 40 (16) :3187-3190