Synthesis of the [7-5-5] tricyclic core of Daphniphyllum alkaloids. Issue 19 (25th April 2018)

• Record Type: Journal Article
• Authors: Kitabayashi, Yusuke; Fukuyama, Tohru; Yokoshima, Satoshi
• Is Part Of: Organic & biomolecular chemistry. Volume 16:Issue 19(2018)
• Page Start: 3556
• Page End: 3559
• Publication Date: 2018-04-25
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c8ob00859k
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : The [7-5-5] tricyclic core of the Daphniphyllum alkaloids was constructed, featuring a Claisen-Ireland rearrangement to install the two contiguous stereogenic centers, E1cB elimination to form the tetrasubstituted C–C double bond, and a 2, 3-Wittig rearrangement to construct the quaternary carbon. Abstract : The [7-5-5] tricyclic core of the Daphniphyllum alkaloids was constructed, featuring a Claisen-Ireland rearrangement to install the two contiguous stereogenic centers, E1cB elimination to form the tetrasubstituted C–C double bond, and a 2, 3-Wittig rearrangement to construct the quaternary carbon. Ring-closing metathesis and an intramolecular carbonyl ene reaction were employed for construction of the requisite ring system.