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Updated: Aug 13, 2025

Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation
Published on: August 1, 2018
Visible-Light-Promoted Tandem Thiol-Ene Click Reaction/Transannular Cyclization and Regioselective Cyclopropane
Neng Wang1, Hang Wang1, Lin-Xi Wan1
1School of Life Science and Engineering, Southwest Jiaotong University, Chengdu, Sichuan 610031, People's Republic of China.
Abstract:
The biorelevant sulfur-containing Euphorbia diterpenes with scarce 5/7/6/3 premyrsinane- and 5/7/6 myrsinane-type backbones were easily constructed from naturally abundant lathyrane-type Euphorbia factor L3 by visible-light-triggered tandem thiol-ene click reaction/transannular cyclization and regioselective cyclopropane ring-opening. The selenide diterpene was also successfully obtained to verify the system universality. This concise synthesis route gives an efficient strategy for obtaining structurally diverse Euphorbia diterpenes under very mild conditions and provides a promising anti-HIV bioactive premyrsinane diterpene 3h.
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Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.