共 62 条
Strategies for the formation of tetrahydropyran rings in the synthesis of natural products
被引:326
作者:

Clarke, Paul A.
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机构:
Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

Santos, Soraia
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h-index: 0
机构:
Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England
机构:
[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England
关键词:
tetrahydropyran;
total synthesis;
natural products;
D O I:
10.1002/ejoc.200500964
中图分类号:
O62 [有机化学];
学科分类号:
070303 ;
081704 ;
摘要:
This microreview surveys the literature over the last five years with regard to construction of functionalised tetrahydropyran (THP) rings in the context of the synthesis of natural products. The overview given is intended to provide a working knowledge of the area for those who are unfamiliar, and to refresh and remind those who do work in the area of the exciting developments in the field. While the construction of the THP rings in a number of natural products has been reviewed, we have attempted to highlight the different strategies by focusing on two natural products, namely phorboxazole and centrolobine as case studies. Over the last five years, these natural products have become a test bed for new methods for the construction of THP rings.
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页码:2045 / 2053
页数:9
相关论文
共 62 条
[1]
Total synthesis of (+)-dactylolide through an efficient sequential peterson olefination and prins cyclization reaction
[J].
Aubele, DL
;
Wan, SY
;
Floreancig, PE
.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2005, 44 (22)
:3485-3488

Aubele, DL
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA

Wan, SY
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA

Floreancig, PE
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
[2]
Two successive one-pot reactions leading to the expeditious synthesis of (-)-centrolobine
[J].
Boulard, L
;
BouzBouz, S
;
Cossy, J
;
Franck, X
;
Figadère, B
.
TETRAHEDRON LETTERS,
2004, 45 (35)
:6603-6605

Boulard, L
论文数: 0 引用数: 0
h-index: 0
机构: CNRS, Chim Organ Lab, ESPCI, F-75231 Paris 05, France

BouzBouz, S
论文数: 0 引用数: 0
h-index: 0
机构: CNRS, Chim Organ Lab, ESPCI, F-75231 Paris 05, France

Cossy, J
论文数: 0 引用数: 0
h-index: 0
机构: CNRS, Chim Organ Lab, ESPCI, F-75231 Paris 05, France

Franck, X
论文数: 0 引用数: 0
h-index: 0
机构: CNRS, Chim Organ Lab, ESPCI, F-75231 Paris 05, France

Figadère, B
论文数: 0 引用数: 0
h-index: 0
机构: CNRS, Chim Organ Lab, ESPCI, F-75231 Paris 05, France
[3]
Reductive cyclizations of hydroxysulfinyl ketones:: Enantioselective access to tetrahydropyran and tetrahydrofuran derivatives
[J].
Carreño, MC
;
Des Mazery, R
;
Urbano, A
;
Colobert, F
;
Solladié, G
.
JOURNAL OF ORGANIC CHEMISTRY,
2003, 68 (20)
:7779-7787

Carreño, MC
论文数: 0 引用数: 0
h-index: 0
机构: Univ Autonoma Madrid, Dept Quim Organ C1, E-28049 Madrid, Spain

Des Mazery, R
论文数: 0 引用数: 0
h-index: 0
机构: Univ Autonoma Madrid, Dept Quim Organ C1, E-28049 Madrid, Spain

Urbano, A
论文数: 0 引用数: 0
h-index: 0
机构: Univ Autonoma Madrid, Dept Quim Organ C1, E-28049 Madrid, Spain

Colobert, F
论文数: 0 引用数: 0
h-index: 0
机构: Univ Autonoma Madrid, Dept Quim Organ C1, E-28049 Madrid, Spain

Solladié, G
论文数: 0 引用数: 0
h-index: 0
机构: Univ Autonoma Madrid, Dept Quim Organ C1, E-28049 Madrid, Spain
[4]
Prins cyclizations in silyl additives with suppression of epimerization: Versatile tool in the synthesis of the tetrahydropyran backbone of natural products
[J].
Chan, KP
;
Loh, TP
.
ORGANIC LETTERS,
2005, 7 (20)
:4491-4494

Chan, KP
论文数: 0 引用数: 0
h-index: 0
机构:
Nanyang Technol Univ, Div Chem & Biol Chem, Singapore 637616, Singapore Nanyang Technol Univ, Div Chem & Biol Chem, Singapore 637616, Singapore

Loh, TP
论文数: 0 引用数: 0
h-index: 0
机构:
Nanyang Technol Univ, Div Chem & Biol Chem, Singapore 637616, Singapore Nanyang Technol Univ, Div Chem & Biol Chem, Singapore 637616, Singapore
[5]
Asymmetric synthesis of the pyran antibiotic (-)-centrolobine
[J].
Chandrasekhar, S
;
Prakash, SJ
;
Shyamsunder, T
.
TETRAHEDRON LETTERS,
2005, 46 (39)
:6651-6653

Chandrasekhar, S
论文数: 0 引用数: 0
h-index: 0
机构:
Indian Inst Chem Technol, Div Organ 1, Hyderabad 500007, Andhra Pradesh, India Indian Inst Chem Technol, Div Organ 1, Hyderabad 500007, Andhra Pradesh, India

Prakash, SJ
论文数: 0 引用数: 0
h-index: 0
机构:
Indian Inst Chem Technol, Div Organ 1, Hyderabad 500007, Andhra Pradesh, India Indian Inst Chem Technol, Div Organ 1, Hyderabad 500007, Andhra Pradesh, India

Shyamsunder, T
论文数: 0 引用数: 0
h-index: 0
机构:
Indian Inst Chem Technol, Div Organ 1, Hyderabad 500007, Andhra Pradesh, India Indian Inst Chem Technol, Div Organ 1, Hyderabad 500007, Andhra Pradesh, India
[6]
The one-pot, multi-component construction of highly substituted tetrahydropyran-4-ones using the Maitland-Japp reaction
[J].
Clarke, PA
;
Martin, WHC
;
Hargreaves, JM
;
Wilson, C
;
Blake, AJ
.
ORGANIC & BIOMOLECULAR CHEMISTRY,
2005, 3 (19)
:3551-3563

Clarke, PA
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

Martin, WHC
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

Hargreaves, JM
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

Wilson, C
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

Blake, AJ
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England
[7]
Exploiting the Maitland-Japp reaction:: a synthesis of (±)-centrolobine
[J].
Clarke, PA
;
Martin, WHC
.
TETRAHEDRON,
2005, 61 (23)
:5433-5438

Clarke, PA
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

Martin, WHC
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England
[8]
Revisiting the Maitland-Japp reaction. Concise construction of highly functionalised tetrahydropyran-4-ones
[J].
Clarke, PA
;
Martin, WHC
;
Hargreaves, JM
;
Wilson, C
;
Blake, AJ
.
CHEMICAL COMMUNICATIONS,
2005, (08)
:1061-1063

Clarke, PA
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

Martin, WHC
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

Hargreaves, JM
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

Wilson, C
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

Blake, AJ
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England
[9]
Synthetic studies on the DEF-rings of FR182877 and hexacyclinic acid
[J].
Clarke, PA
;
Grist, M
;
Ebden, M
;
Wilson, C
;
Blake, AJ
.
TETRAHEDRON,
2005, 61 (02)
:353-363

Clarke, PA
论文数: 0 引用数: 0
h-index: 0
机构: Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

Grist, M
论文数: 0 引用数: 0
h-index: 0
机构: Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

Ebden, M
论文数: 0 引用数: 0
h-index: 0
机构: Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

Wilson, C
论文数: 0 引用数: 0
h-index: 0
机构: Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

Blake, AJ
论文数: 0 引用数: 0
h-index: 0
机构: Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England
[10]
An expedient synthesis of (±)-centrolobine
[J].
Clarke, PA
;
Martin, WHC
.
TETRAHEDRON LETTERS,
2004, 45 (49)
:9061-9063

Clarke, PA
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

Martin, WHC
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England