Synthetic approaches to the daphnane and tigliane diterpenes from aromatic precursors. Issue 32 (9th August 2019)

• Record Type: Journal Article
• Authors: Brill, Zachary G.; Zhao, Yu-Ming; Vasilev, Vasil H.; Maimone, Thomas J.
• Is Part Of: Tetrahedron. Volume 75:Issue 32(2019)
• Page Start: 4212
• Page End: 4221
• Publication Date: 2019-08-09
• Subjects: Terpene -- Total synthesis -- Natural product -- Cascade reaction; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2019.04.058
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Synthetic studies toward the daphnane and tigliane diterpenes, a large family of natural products from the plant families Euphorbiaceae and Thymelaeaceae, are reported. Retrosynthetic analysis traced these molecules back to an aromatic precursor and several routes were explored in the forward direction to access such motifs. Two strategies ultimately proved capable of forging complex 5, 7, 6 -fused tricyclic ring systems, one of which proceeded in only seven steps. Graphical abstract: Image 1