Halogenated oxabicyclo[3.2.1]octadiene building blocks: Elaboration of the dibromoenone

被引：12

作者：

Pelphrey, PM ^{[1
]}

Orugunty, RS

Helmich, RJ

Battiste, MA

Wright, DL

机构：

[1] Dartmouth Coll, Dept Chem, Hanover, NH 03755 USA

[2] Univ Florida, Dept Chem, Gainesville, FL 32611 USA

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 2005卷 / 20期

关键词：

cross-coupling; dibromoenone; oxygen heterocycles; palladium;

D O I：

10.1002/ejoc.200500529

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have been interested in exploiting the highly functionalized oxabicyclo[3.2.1]octadienes that are produced by the cycloaddition of furan and tetrabromocyclopropene as synthetic building blocks. As part of this program, we have prepared non-racemic derivatives of these adducts containing an alpha,beta-dibromoenone moiety embedded in the bicyclic framework. Elaboration of this unit has been realized through substitution and palladium-catalyzed cross-coupling reactions. Formation of bicyclodecenes has also been accomplished by a chromium-nickel-mediated ring closure. (c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.

引用

页码：4296 / 4303

页数：8

共 32 条

[21] Halogenated building blocks for 2D crystal engineering on solid surfaces: lessons from hydrogen bonding
Mukherjee, Arijit
Sanz-Matias, Ana
Velpula, Gangamallaiah
Waghray, Deepali
Ivasenko, Oleksandr
Bilbao, Nerea
Harvey, Jeremy N.
Mali, Kunal S.
De Feyter, Steven
CHEMICAL SCIENCE, 2019, 10 (13) : 3881 - 3891
[22] Synthesis of 4-Halogenated 3-Fluoro-6-methoxyquinolines: Key Building Blocks for the Synthesis of Antibiotics
Flagstad, Thomas
Petersen, Mette T.
Hinnerfeldt, Daniel M.
Givskov, Michael
Nielsen, Thomas E.
SYNTHESIS-STUTTGART, 2014, 46 (23): : 3263 - 3267
[23] Cyclopropyl building blocks for organic synthesis, 38 -: Highly functionalized bicyclo[3.2.1]octane derivatives from readily available 2′-alkoxytricyclo[3.2.1.02,7]octanes:: Building blocks for terpenes, Part I
de Meijere, A
Hadjiarapoglou, L
Noltemeyer, M
Gutke, HJ
Klein, I
Spitzner, D
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 1998, 1998 (03) : 441 - 451
[24] Halogenated Anthracenes as Building Blocks for the On-Surface Synthesis of Covalent Polymers: Structure Prediction with the Lattice Monte Carlo Method
Lisiecki, Jakub
Szabelski, Pawel
JOURNAL OF PHYSICAL CHEMISTRY C, 2021, 125 (29): : 15934 - 15949
[25] Synthesis of the C17-C23 subunit of ionomycin from C1-functionalized 8-oxabicyclo[3.2.1]oct-6-en-3-one.: New synthetic methodology to prepare polyfunctionalized heptane building blocks with four stereocenters
Montaña, AM
García, F
Grima, PM
TETRAHEDRON, 1999, 55 (17) : 5483 - 5504
[26] BICYCLO[3.2.1]OCTENONES AS BUILDING-BLOCKS IN NATURAL-PRODUCTS SYNTHESIS .2. FORMAL SYNTHESIS OF (PLUS-OR-MINUS)-VERBENALOL
CHANG, CP
HSU, LF
CHANG, NC
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (07): : 1898 - 1899
[27] BICYCLO[3.2.1]OCTENONES AS BUILDING-BLOCKS IN NATURAL-PRODUCTS SYNTHESIS .3. TOTAL SYNTHESIS OF (+/-)-10-DEOXYGENIPOSIDE AGLUCONE
HSU, LF
CHANG, NC
JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 1994, 41 (05) : 609 - 611
[28] Ground and excited state electronic properties of halogenated tetraarylporphyrins. Tuning the building blocks for porphyrin-based photonic devices
Yang, SI
Seth, J
Strachan, JP
Gentemann, S
Kim, D
Holten, D
Lindsey, JS
Bocian, DF
JOURNAL OF PORPHYRINS AND PHTHALOCYANINES, 1999, 3 (02) : 117 - 147
[29] BICYCLO[3.2.1]OCTENONES AS BUILDING-BLOCKS IN NATURAL-PRODUCTS SYNTHESIS .1. FORMAL SYNTHESIS OF (+/-)-MUSSAENOSIDE AND (+/-)-8-EPILOGANIN AGLUCONES
HSU, LF
CHANG, CP
LI, MC
CHANG, NC
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (17): : 4756 - 4757
[30] Sugar-derived building blocks, part 30.: A 2-C-fructosyl-propanone locked in a 2,7-dioxabicyclo[3.2.1]octane framework
Peters, S
Lichtenthaler, FW
Lindner, HJ
TETRAHEDRON-ASYMMETRY, 2003, 14 (16) : 2475 - 2479

← 1 2 3 4 →