Concise and Practical Total Synthesis of (+)-Abscisic Acid | Zendy

Dahye Kim | Zendy; Sangho Koo | Zendy

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Concise and Practical Total Synthesis of (+)-Abscisic Acid

Author(s) -

Dahye Kim,

Sangho Koo

Publication year - 2020

Publication title -

acs omega

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.779

H-Index - 40

ISSN - 2470-1343

DOI - 10.1021/acsomega.0c01332

Subject(s) - abscisic acid , decarboxylation , yield (engineering) , chemistry , total synthesis , malonate , conjugated system , malonic acid , organic chemistry , stereochemistry , catalysis , biochemistry , materials science , polymer , metallurgy , gene

(+)-Abscisic acid 1 was obtained in a concise total synthesis from ethyl 2,6,6-trimethyl-4-oxocyclohex-2-ene-1-carboxylate ( 2 ) with 41% overall yield in seven steps. A hydroxyl group was stereoselectively introduced by Sharpless asymmetric epoxidation; then, the side chain was appended with dimethyl 2-(propan-2-ylidene)malonate ( 7 ); subsequently, selective decarboxylation of diacid 8 established the Z -configuration of the conjugated acid 1 .

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