Elaboration of D-(-)-ribose into a tricyclic, natural product-like scaffold

被引：17

作者：

Messer, R ^{[1
]}

Schmitz, A ^{[1
]}

Moesch, L ^{[1
]}

Häner, R ^{[1
]}

机构：

[1] Univ Bern, Dept Chem & Biochem, CH-3012 Bern, Switzerland

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 24期

关键词：

D O I：

10.1021/jo048351+

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The construction of natural product-like, tricyclic compounds is reported. Starting from a D-(-)-ribose-derived dihydrofurane, the tricyclic scaffold is prepared via an intramolecular hetero-Diels-Alder reaction. The reaction proceeds with very high diastereoselectivity through an endo transition state, as established on the basis of X-ray structural analysis of the products. Further modification and derivatization of the obtained products is described.

引用

页码：8558 / 8560

页数：3

共 50 条

[31] Rapid and diverse route to natural product-like biaryl ether containing macrocycles
Cristau, P
Vors, JP
Zhu, JP
TETRAHEDRON, 2003, 59 (40) : 7859 - 7870
[32] Natural Product-Like Virtual Libraries: Recursive Atom-Based Enumeration
Yu, Melvin J.
JOURNAL OF CHEMICAL INFORMATION AND MODELING, 2011, 51 (03) : 541 - 557
[33] Chemical variation of natural product-like scaffolds: design and synthesis of spiroketal derivatives
Zinzalla, G
Milroy, LG
Ley, SV
ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (10) : 1977 - 2002
[34] Design and synthesis of a natural product-like macrocycle library containing tetrahydropyran moieties
Lee, Hyunji
Hong, Jiyong
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 256
[35] A versatile strategy for divergent and diastereoselective synthesis of natural product-like polyhydroxylated indolizidines
Jiang, Xiao-Ping
Cheng, Ying
Shi, Gao-Feng
Kang, Zhi-Mei
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (06): : 2212 - 2215
[36] Synthesis of natural product-like polyprenylated phenols and quinones: Evaluation of their neuroprotective activities
Kamauchi, Hitoshi
Oda, Takumi
Horiuchi, Kanayo
Takao, Koichi
Sugita, Yoshiaki
BIOORGANIC & MEDICINAL CHEMISTRY, 2020, 28 (01)
[37] Synthesis and biological evaluation of natural product-like macrocycles containing integral carbohydrate moieties
Desmond, Richard T.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244
[38] Ribosomal production and in vitro selection of natural product-like peptidomimetics: The FIT and RaPID systems
Hipolito, Christopher J.
Suga, Hiroaki
CURRENT OPINION IN CHEMICAL BIOLOGY, 2012, 16 (1-2) : 196 - 203
[39] Solid-phase iminium cyclization reactions for the synthesis of natural product-like diketopiperazines
Petersen, Rico
Le Quement, Sebastian T.
Nielsen, Thomas E.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
[40] Diversity oriented synthesis and branching reaction pathway to generate natural product-like compounds
Liao, Y
Hu, YH
Wu, H
Zhu, Q
Donovan, M
Fathi, R
Yang, Z
CURRENT MEDICINAL CHEMISTRY, 2003, 10 (21) : 2285 - 2316

← 1 2 3 4 5 →