Total Synthesis of Diterpenoid Steenkrotin A1. (20th April 2015)

• Record Type: Journal Article
• Authors: Pan, Saiyong; Xuan, Jun; Gao, Beiling; Zhu, An; Ding, Hanfeng
• Is Part Of: Angewandte Chemie. Volume 127:Number 23(2015)
• Page Start: 7009
• Page End: 7012
• Publication Date: 2015-04-20
• Subjects: Aldolreaktionen -- Carbenoide -- Naturstoffe -- Radikalreaktionen -- Totalsynthese; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201502034
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: A concise and diastereoselective total synthesis of the diterpenoid (±)‐steenkrotin A is described for the first time. The strategy mainly features three key ring formations: 1) a rhodium‐catalyzed OH bond insertion followed by an intramolecular carbonyl‐ene reaction to build up the tetrahydrofuran subunit; 2) sequential SmI2 ‐mediated Ueno–Stork and ketyl–olefin cyclizations to construct the [5, 7] spirobicyclic skeleton; and 3) an intramolecular aldol condensation/vinylogous retro‐aldol/aldol sequence to form the final six‐membered ring with inversion of the relative configuration at the C7 position.