Chiral synthesis via organoboranes. 7. Diastereoselective and enantioselective synthesis of erythro- and threo-.beta.-methylhomoallyl alcohols via enantiomeric (Z)- and (E)-crotylboranes

1986 ◽  
Vol 108 (19) ◽  
pp. 5919-5923 ◽  
Author(s):  
Herbert C. Brown ◽  
Krishna S. Bhat
Keyword(s):  
Enantioselective Synthesis ◽  
Chiral Synthesis

Enantioselective synthesis of an octahydroindolizine (indolizidine) alcohol using an enzymatic resolution

2017 ◽  
Vol 15 (14) ◽  
pp. 2953-2961 ◽  
Author(s):  
Jing Zhang ◽  
Rao Kolluri ◽  
Salvador G. Alvarez ◽  
Mark M. Irving ◽  
Rajinder Singh ◽  
...  
Keyword(s):  
Pharmaceutical Industry ◽  
Building Blocks ◽  
Enantioselective Synthesis ◽  
Chiral Synthesis ◽  
Enzymatic Resolution

A homo-chiral synthesis of (7R,8aS)-octahydro-5,5-dimethylindolizin-7-amine 8 and (7S,8aS)-octahydro-5,5-dimethylindolizin-7-ol 9, amine building blocks which have found applications within the pharmaceutical industry, is presented.

Chiral synthesis of (+)-8′-demethyl abscisic acid

1996 ◽  
Vol 74 (10) ◽  
pp. 1836-1843 ◽  
Author(s):  
Patricia A. Rose ◽  
Bo Lei ◽  
Angela C. Shaw ◽  
Suzanne R. Abrams ◽  
M. K. Walker-Simmons ◽  
...  
Keyword(s):  
Biological Activity ◽  
Abscisic Acid ◽  
Enantioselective Synthesis ◽  
Phenol Oxidation ◽  
Germination Inhibition ◽  
Embryo Germination ◽  
Chiral Synthesis ◽  
Wheat Embryo ◽  
Methyl Group ◽  
Key Words Abscisic Acid

An enantioselective synthesis of (+)-8′-demethyl ABA (2) is described. The chiral intermediate 7 was prepared by yeast reduction of a substituted monoprotected cyclohexa-2,5-dien-1,4-dione (9) synthesized through a phenol oxidation. The scope and limitations of the phenol oxidation is described. 8′-Demethyl ABA shows ABA-like activity in wheat embryo germination inhibition, showing that the 8′-methyl group is not essential for biological activity. Key words: abscisic acid, phenol oxidation, yeast reduction.

Catalytic enantioselective synthesis of indolizino[8,7-b]indole alkaloid derivatives based on the tandem reaction of tertiary enamides

2021 ◽  
Author(s):  
Xin-Ming Xu ◽  
Ming Xie ◽  
Jiazhu Li ◽  
Mei-Xiang Wang
Keyword(s):  
Indole Alkaloid ◽  
Enantioselective Synthesis ◽  
High Yield ◽  
Tandem Reaction ◽  
Indole Derivatives

An exquisite Pybox/Cu(OTf)2-catalyzed asymmetric tandem reaction of tertiary enamides was developed, which enabled the expeditious synthesis of indolizino[8,7-b]indole derivatives in high yield, excellent enantioselectivity and diastereoselectivity.

Sign in / Sign up

Export Citation Format

Share Document