A Catalytic Enantioselective Synthesis of the Endothelin Receptor Antagonists SB-209670 and SB-217242. A Base-Catalyzed Stereospecific Formal 1,3-Hydrogen Transfer of a Chiral 3-Arylindenol

Clark, William M.; Tickner-Eldridge, Ann M.; Huang, Guobao; Pridgen, Lendon N.; Olsen, Mark A.; Mills, Robert J.; Lantos, and Ivan; Baine, Neil H.

doi:10.1021/ja973882j

Cited by 123 publications

(44 citation statements)

References 13 publications

(12 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[8] Some years ago, Clark et al reported a novel enantioselective synthesis of highly enantioenriched 3-arylindanones via three consecutive, base-induced [1,5]-suprafacial sigmatropic rearrangements of the corresponding 3-arylindenol, easily available by catalytic asymmetric methyloxazaborolidine (Me-CBS) reduction of the indenone. [9] By adopting this approach, we would be able to access the dihydrochromen-2-one 7 via a Baeyer-Villiger oxidation (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

Catalytic Asymmetric Total Synthesis of the Muscarinic Receptor Antagonist (R)-Tolterodine

Hedberg

Andersson

2005

Advanced Synthesis & Catalysis

View full text Add to dashboard Cite

A convenient and high yielding method for the preparation of (R)-tolterodine, utilizing a catalytic asymmetric Me-CBS reduction was developed. Highly enantioenriched (R)-6-methyl-4-phenyl-3,4-dihydrochromen-2-one (94% ee) was recrystallized to yield practically enantiopure material (ee > 99%) and converted to (R)-tolterodine in a four-step procedure. The configuration of the crucial stereocenter was preserved during the synthesis and the obtained product was identified by chiral HPLC to be the (R)-tolterodine enantiomer.

show abstract

Section: Resultsmentioning

confidence: 99%

Catalytic Asymmetric Total Synthesis of the Muscarinic Receptor Antagonist (R)-Tolterodine

Hedberg

Andersson

2005

Advanced Synthesis & Catalysis

View full text Add to dashboard Cite

show abstract

“…We also prepared the samples of non-peptide endothelin receptor antagonists SB209670 [31,32], JMF310 [33], and YHK891 [34]. The active herbal components, Magnolol, Geniposide and Honokiol, were purchased from Wako Pure Chemical Industries (Japan).…”

Section: Samples and Reagentsmentioning

confidence: 99%

Capillary electrophoresis using immobilized whole cells with overexpressed endothelin receptor for specific ligand screening

Yu¹,

Tseng²,

Fang³

et al. 2004

Electrophoresis

View full text Add to dashboard Cite

A new capillary electrophoresis method using immobilized cells as the stationary phase has been developed. The power of this method is demonstrated by the separation and identification of endothelin antagonists on a capillary column coated by the transfected Chinese hamster ovary (CHO) cells with overexpressing endothelin receptors. The screening results are validated by functional assays suppressing the increase of intracellular calcium concentration induced by endothelin-1. Instead of making efforts in isolating protein receptors, the easily prepared whole-cell capillary column provides a superior tool on the basis of ligand/receptor affinity for a rapid screening of potent drug candidates from compound libraries.

show abstract

“…Indenones have been used as starting materials for the synthesis of various bioactive products such as C-nor-D-homosteroids, 3 estrogen-binding receptors, 4 gibberellins, 5 and more recently non-peptidic antagonists of endothelin receptors (Scheme 1). 6 Indenones have also been used for the synthesis of compounds such as indanones, photochromic indenone oxides, 7 2,4-and 3,4-disubstituted 1-naphthols 8 (Scheme 1). The indenone unit is also present in a few natural products.…”

Section: Introductionmentioning

confidence: 99%

Chemistry of 3-arylindenones: behavior in superacids and photodimerization

et al. 2005

View full text Add to dashboard Cite

A Catalytic Enantioselective Synthesis of the Endothelin Receptor Antagonists SB-209670 and SB-217242. A Base-Catalyzed Stereospecific Formal 1,3-Hydrogen Transfer of a Chiral 3-Arylindenol

Cited by 123 publications

References 13 publications

Catalytic Asymmetric Total Synthesis of the Muscarinic Receptor Antagonist (R)-Tolterodine

Catalytic Asymmetric Total Synthesis of the Muscarinic Receptor Antagonist (R)-Tolterodine

Capillary electrophoresis using immobilized whole cells with overexpressed endothelin receptor for specific ligand screening

Chemistry of 3-arylindenones: behavior in superacids and photodimerization

Contact Info

Product

Resources

About