𝔖 Bobbio Scriptorium
✦   LIBER   ✦

An Enantioselective Total Synthesis of Natural (+)-Luciduline

✍ Scribed by Wolfgang Oppolzer; Martin Petrzilka

Publisher
John Wiley and Sons
Year
1978
Tongue
German
Weight
497 KB
Volume
61
Category
Article
ISSN
0018-019X

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

The naturally occurring Lycopodium alkaloid (+)‐luciduline (1) has been synthesized from (R)‐5‐methyl‐cyclohex‐2‐en‐1‐one (12) by a sequence of seven steps (s. Scheme 6) in 33% overall yield. The key step 4β†’6 presumably involves a transient nitrone 5 which undergoes a highly regioselective intramolecular addition to a non‐polarized olefinic bond.

πŸ“œ SIMILAR VOLUMES

Enantioselective total synthesis of natu
Enantioselective total synthesis of natural 11,12-epoxycembrene-C
✍ Yulin Li; Zuosheng Liu; Jiong Lan; Jing Li; Lizeng Peng; Weidong Z Li; Ying Li; πŸ“‚ Article πŸ“… 2000 πŸ› Elsevier Science 🌐 French βš– 120 KB

The first enantioselective total synthesis of (+)-11,12-epoxycembrene-C (1), a novel naturally occurring cembranoxide isolated from tropical marine soft coral, was achieved via a general approach by employing an intramolecular McMurry coupling and Sharpless asymmetric epoxidation as key steps from r