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

Dahye Kim; Sangho Koo

doi:10.1021/acsomega.0c01332

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

ACS Omega. 2020 May 29;5(22):13296-13302. doi: 10.1021/acsomega.0c01332. eCollection 2020 Jun 9.

Authors

Dahye Kim¹, Sangho Koo^{1

2}

Affiliations

¹ Department of Energy Science and Technology, Myongji University, Myongji-Ro 116, Cheoin-Gu, Yongin, Gyeonggi-Do 17058, Korea.
² Department of Chemistry, Myongji University, Myongji-Ro 116, Cheoin-Gu, Yongin, Gyeonggi-Do 17058, Korea.

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.