Total Synthesis of Isorosthin L and Isoadenolin I

Junli Ao; Chao Sun; Bolin Chen; Na Yu; Guangxin Liang

doi:10.1002/anie.202114489

Total Synthesis of Isorosthin L and Isoadenolin I

Angew Chem Int Ed Engl. 2022 Mar 1;61(10):e202114489. doi: 10.1002/anie.202114489. Epub 2022 Jan 14.

Authors

Junli Ao^{1

2}, Chao Sun², Bolin Chen¹, Na Yu², Guangxin Liang²

Affiliations

¹ State Key Laboratory of Elemento-organic Chemistry, College of Chemistry, Nankai University, Tianjin, 300071, China.
² School of Physical Science and Technology, ShanghaiTech University, Shanghai, 201210, China.

PMID: 34773349
DOI: 10.1002/anie.202114489

Abstract

Total syntheses of two Isodon diterpenes, isorosthin L and isoadenolin I, are reported. The synthetic strategy features a quick assembly of two simple building blocks through a diastereoselective intermolecular aldol reaction and a subsequent radical cyclization for efficient construction of a rather complex advanced intermediate bearing a quaternary stereocenter present in all Isodon diterpenes. Oxidative cleavage of the C-C bond in the cyclopentane enabled the conversion to a lactone moiety which is desired for the construction of the molecular skeleton through reductive coupling with an aldehyde carbonyl group.

Keywords: Aldol reaction; Natural products; Radical cyclization; Total synthesis; ent-Kaurane diterpenoids.

Publication types

Research Support, Non-U.S. Gov't