Beyond catalyst deactivation: cross-metathesis involving olefins containing N-heteroaromatics

• Kevin Lafaye,
• Cyril Bosset,
• Lionel Nicolas,
• Amandine Guérinot and
• Janine Cossy

Beilstein J. Org. Chem. 2015, 11, 2223–2241, doi:10.3762/bjoc.11.241

• ). One of the rare successful example of CM involving alkene containing a pyridine moiety was reported by Sarpong et al. in their total synthesis of (±)-lyconadin A [77]. Alkene 91 was coupled with ethyl acrylate (5 equiv) using a catalytic amount of the G-HII catalyst to give 92 with a very good yield

Exploration of an epoxidation–ring-opening strategy for the synthesis of lyconadin A and discovery of an unexpected Payne rearrangement

• Brad M. Loertscher,
• Yu Zhang and
• Steven L. Castle

Beilstein J. Org. Chem. 2013, 9, 1179–1184, doi:10.3762/bjoc.9.132

• Brad M. Loertscher Yu Zhang Steven L. Castle Department of Chemistry and Biochemistry, Brigham Young University, C100 BNSN, Provo, UT, 84602, USA 10.3762/bjoc.9.132 Abstract In the context of synthetic efforts targeting the alkaloid lyconadin A, scalemic epoxide 25 was prepared by a highly

• . Keywords: Lewis acid; lyconadin A; Myers alkylation; Payne rearrangement; Shi epoxidation; Introduction Lyconadin A (1, Figure 1) was isolated from the club moss Lycopodium complanatum in 2001 by Kobayashi and co-workers [1]. Subsequent to this discovery, lyconadins B–F were isolated and characterized [2

• addition to its interesting bioactivity, lyconadin A presents a significant synthetic challenge by virtue of its unique pentacyclic skeleton, which contains six stereocenters and a pyridone ring. It is therefore not surprising that 1 has attracted the attention of the organic synthesis community. The first