Synthesis of the azaspiracid-1 trioxadispiroketal

被引：43

作者：

Geisler, LK ^{[1
]}

Nguyen, S ^{[1
]}

Forsyth, CJ ^{[1
]}

机构：

[1] Univ Minnesota, Inst Technol, Dept Chem, Minneapolis, MN 55113 USA

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 23期

关键词：

D O I：

10.1021/ol048581a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The de novo analysis, design, and synthesis of the azaspiracid-1 trioxadispiroketal system is described. A revised structural model was developed on the basis of an independent analysis of the NMR spectral data of the natural product that fit all of the data and the thermodynamically favored spiroketal paradigm. This model was then tested via synthesis using a novel trioxadispiroketalization process and supported by spectroscopic correlation.

引用

页码：4159 / 4162

页数：4

共 33 条

[1] Synthesis of a 2,9-dioxabicyclo[3.3.1]nonane via double intramolecular hetero-Michael addition: Entry to the F-G ring system of the azaspiracids [J].

Aiguade, J ;

Hao, JL ;

Forsyth, CJ .

ORGANIC LETTERS, 2001, 3 (07) :979-982

[2] DIRECT EVIDENCE SUPPORTING A SINGLE-ELECTRON TRANSFER PATHWAY IN THE REDUCTION OF KETONES BY PRIMARY, SECONDARY, AND TERTIARY GRIGNARD-REAGENTS [J].

ASHBY, EC ;

GOEL, AB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (16) :4983-4985

[3]

Bohner TV, 1999, HELV CHIM ACTA, V82, P143, DOI 10.1002/(SICI)1522-2675(19990210)82:2<143::AID-HLCA143>3.0.CO

[4]

2-0

[5] Controlling influences in bisspiroketal formation: synthesis of the ABC ring system of azaspiracid [J].

Carter, RG ;

Bourland, TC ;

Zhou, XT ;

Gronemeyer, MA .

TETRAHEDRON, 2003, 59 (45) :8963-8974

[6] Synthesis of the ABC ring system of azaspiracid. 1. Effect of D ring truncation on bis-spirocyclization [J].

Carter, RG ;

Bourland, TC ;

Graves, DE .

ORGANIC LETTERS, 2002, 4 (13) :2177-2179

[7] Synthesis of the ABC ring system of azaspiracid.: 2.: A systematic study into the effect of C16 and C17 substitution on bis-spirocyclization [J].

Carter, RG ;

Graves, DE ;

Gronemeyer, MA ;

Tschumper, GS .

ORGANIC LETTERS, 2002, 4 (13) :2181-2184

[8] Studies directed toward the total synthesis of azaspiracid:: Stereoselective construction of C1-C12, C13-C19, and C21-C25 fragments [J].

Carter, RG ;

Weldon, DJ .

ORGANIC LETTERS, 2000, 2 (24) :3913-3916

[9] Studies directed toward the total synthesis of azaspiracid.: Construction of the C1-C19 carbon backbone and synthesis of the C10, C13 nonnatural transoidal bisspirocyclic ring system [J].

Carter, RG ;

Graves, DE .

TETRAHEDRON LETTERS, 2001, 42 (35) :6035-6039

[10] Direct synthesis of substituted tetrahydrofurans via regioselective dehydrative polyol cyclization cascades [J].

Dounay, AB ;

Florence, GJ ;

Saito, A ;

Forsyth, CJ .

TETRAHEDRON, 2002, 58 (10) :1865-1874

← 1 2 3 4 →