Collective total synthesis of botryanes. Issue 12 (22nd March 2019)

• Record Type: Journal Article
• Authors: Qiao, Chuang; Zhang, Wen; Han, Jing-Chun; Dai, Wei-Min; Li, Chuang-Chuang
• Is Part Of: Tetrahedron. Volume 75:Issue 12(2019)
• Page Start: 1739
• Page End: 1745
• Publication Date: 2019-03-22
• Subjects: Intramolecular Diels-Alder reaction -- Botryanes -- Hypocrolide A -- Collective total synthesis; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2018.11.019
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: The collective total synthesis of a series of botryanes, which are an important group of sesquiterpene antibiotics isolated from the metabolites of the fungus Botrytis cinerea, has been reported. The highly functionalized hydrindane skeleton of the botryanes was efficiently synthesized via an unusual intramolecular Diels-Alder reaction, which was promoted by TsOH as a protic acid. The concise total synthesis of (±)-hypocrolide A with a challenging hexacyclic skeleton was accomplished in 8 steps from the readily available starting materials. Graphical abstract: Image 1