Literature DB >> 19360170

Design and synthesis of (E)-1-((3-ethyl-2,4,4-trimethylcyclohex-2-enylidene)methyl-4-substituted benzenes from 1-(2,6,6-trimethylcyclohex-1-enyl)ethanol.

Bhaskar C Das1, Sakkarapalayam M Mahalingam, Todd Evans, George W Kabalka, J Anguiano, K Hema.   

Abstract

A novel strategy for synthesizing (E)-1-((3-ethyl-2,4,4-trimethylcyclohex-2-enylidene)methyl-4-substituted benzenes from 1-(2,6,6-trimethylcyclohex-1-enyl)ethanol has been developed; the allylic alcohol was treated with PPh(3).HBr in methanol followed by aldehydes in the presence of a base and furnished the 1,3-dienes in moderate to good yields (79-86%).

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Year:  2009        PMID: 19360170      PMCID: PMC3140768          DOI: 10.1039/b823063c

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  8 in total

1.  Salt effects on Diels-Alder reaction kinetics.

Authors:  A Kumar
Journal:  Chem Rev       Date:  2001-01       Impact factor: 60.622

2.  Tandem Dielsminus signAlder Cycloadditions in Organic Synthesis.

Authors:  Jeffrey D. Winkler
Journal:  Chem Rev       Date:  1996-02-01       Impact factor: 60.622

Review 3.  Biosynthetic and biomimetic electrocyclizations.

Authors:  Christopher M Beaudry; Jeremiah P Malerich; Dirk Trauner
Journal:  Chem Rev       Date:  2005-12       Impact factor: 60.622

4.  Synthesis of highly substituted 1,3-dienes and 1,3,5-trienes by the palladium-catalyzed coupling of vinylic halides, internal alkynes, and organoboranes.

Authors:  Xiaoxia Zhang; Richard C Larock
Journal:  Org Lett       Date:  2003-08-21       Impact factor: 6.005

5.  Palladium-catalyzed cross-coupling reaction of bis(pinacolato)diboron with 1-alkenyl halides or triflates: convenient synthesis of unsymmetrical 1,3-dienes via the borylation-coupling sequence.

Authors:  Jun Takagi; Kou Takahashi; Tatsuo Ishiyama; Norio Miyaura
Journal:  J Am Chem Soc       Date:  2002-07-10       Impact factor: 15.419

6.  Continuous treatment with all-trans retinoic acid causes a progressive reduction in plasma drug concentrations: implications for relapse and retinoid "resistance" in patients with acute promyelocytic leukemia.

Authors:  J Muindi; S R Frankel; W H Miller; A Jakubowski; D A Scheinberg; C W Young; E Dmitrovsky; R P Warrell
Journal:  Blood       Date:  1992-01-15       Impact factor: 22.113

7.  Highly stereoselective 6pi electrocyclization of bridged bicyclic 1,3,5-trienes.

Authors:  Chantel L Benson; F G West
Journal:  Org Lett       Date:  2007-05-26       Impact factor: 6.005

8.  Conformationally restricted retinoids.

Authors:  M I Dawson; P D Hobbs; K Derdzinski; R L Chan; J Gruber; W R Chao; S Smith; R W Thies; L J Schiff
Journal:  J Med Chem       Date:  1984-11       Impact factor: 7.446

  8 in total
  8 in total

1.  Design and synthesis of novel derivatives of all-trans retinoic acid demonstrate the combined importance of acid moiety and conjugated double bonds in its binding to PML-RAR-alpha oncogene in acute promyelocytic leukemia.

Authors:  Carolina Schinke; Swati Goel; Tushar D Bhagat; Li Zhou; Yongkai Mo; Robert Gallagher; George W Kabalka; Leonidas C Platanias; Amit Verma; Bhaskar Das
Journal:  Leuk Lymphoma       Date:  2010-06

2.  Design and Synthesis of Potential New Apoptosis Agents: Hybrid Compounds Containing Perillyl Alcohol and New Constrained Retinoids.

Authors:  Bhaskar C Das; Sakkarapalayam M Mahalingam; Lipsa Panda; Bo Wang; Phillp Campbell; Todd Evans
Journal:  Tetrahedron Lett       Date:  2010-03-17       Impact factor: 2.415

3.  Radiolabeling and initial biological evaluation of [18F]KBM-1 for imaging RAR-α receptors in neuroblastoma.

Authors:  Kiran Kumar Solingapuram Sai; Bhaskar C Das; Anirudh Sattiraju; Frankis G Almaguel; Suzanne Craft; Akiva Mintz
Journal:  Bioorg Med Chem Lett       Date:  2017-02-01       Impact factor: 2.823

4.  Design and Synthesis of 3,5-Disubstituted 1,2,4-Oxadiazole Containing Retinoids from a Retinoic Acid Receptor Agonist.

Authors:  Bhaskar C Das; Xiang-Ying Tang; Swarnava Sanyal; Seetaram Mohapatra; Patrick Rogler; Sabita Nayak; Todd Evans
Journal:  Tetrahedron Lett       Date:  2011-05-11       Impact factor: 2.415

5.  Design, synthesis and biological study of pinacolyl boronate-substituted stilbenes as novel lipogenic inhibitors.

Authors:  Bhaskar C Das; Xiaoping Zhao; Xiang-Ying Tang; Fajun Yang
Journal:  Bioorg Med Chem Lett       Date:  2011-06-28       Impact factor: 2.823

6.  A forward chemical screen in zebrafish identifies a retinoic acid derivative with receptor specificity.

Authors:  Bhaskar C Das; Kellie McCartin; Ting-Chun Liu; Randall T Peterson; Todd Evans
Journal:  PLoS One       Date:  2010-04-02       Impact factor: 3.240

7.  Design and synthesis of boron containing potential pan-RAR inverse agonists.

Authors:  Bhaskar C Das; Xiang-Ying Tang; Todd Evans
Journal:  Tetrahedron Lett       Date:  2012-01-03       Impact factor: 2.415

8.  Small molecules targeting LapB protein prevent Listeria attachment to catfish muscle.

Authors:  Ali Akgul; Nawar Al-Janabi; Bhaskar Das; Mark Lawrence; Attila Karsi
Journal:  PLoS One       Date:  2017-12-18       Impact factor: 3.240

  8 in total

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