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

ABSTRACT: (+)-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.

SUBMITTER: Kim D

PROVIDER: S-EPMC7288699 | biostudies-literature | 2020 Jun

REPOSITORIES: biostudies-literature

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

Kim Dahye D Koo Sangho S

ACS omega 20200529 22

(+)-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. ...[more]

PMID: 32548516

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