Total synthesis of pteridic acid A.
A convergent approach to the total synthesis of pteridic acid A, having potent plant growth regulator activity, is described. Key steps include the desymmetrization of bicyclic olefin with Brown's chiral hydroboration, acid-mediated spiroketalization, and zirconium-catalyzed ethylmagnesation protocol to install the ethyl stereocenter at C14.
Yadav
J S
JS
Organic Chemistry Division-1, Indian Institute of Chemical Technology, Hyderabad 500 007, India. yadaVpub@iict.res.in
Rajender
V
V
Rao
Y Gangadhara
YG
D006538:Heptanoic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D010937:Plant Growth Regulators / Q000138:chemical synthesis / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D006538:Heptanoic Acids; D010937:Plant Growth Regulators; D013141:Spiro Compounds; C467219:pteridic acid A