Concepedia

A new and short method for the synthesis of 2,4-methanoproline

Thomas Rammeloo, Christian V. Stevens

Chemical Communications · 2002 · 31 citations · 17 references

DOI

Concepts

Abstract

2,4-Methanoproline, a supposed non-proteinogenic anti-feedant, was synthesised in 5 steps starting from allyl benzyl ether 3 in 10% overall yield with an intramolecular nucleophilic substitution as the key step for the formation of the bicyclic skeleton.

References

17

2,4-Methanoproline (2-carboxy-2,4-methanopyrrolidine) and 2,4-methanoglutamic acid (1-amino-1,3-dicarboxycyclobutane) in seeds of Ateleia herbert smithii Pittier (Leguminosae)

E.Arthur Bell, M.Yasin Qureshi, Robert J. Pryce et al. · Journal of the American Chemical Society · 1980 · 94 citations

, , +5

Synthesis of 6-Aza-bicyclo[3,2,1]octan-3-ones via Vinylogous Imide Photochemistry:  An Approach to the Synthesis of the Hetisine Alkaloids

Young‐Shin Kwak, Jeffrey D. Winkler · Journal of the American Chemical Society · 2001 · 70 citations

, , +11

Total Synthesis of 2,4-methanaproline

Michael C. Pirrung · Tetrahedron Letters · 1980 · 66 citations

, , +6

Synthesis of 2,4-methanoproline

Philip F. Hughes, Michael Martin, Jon Clardy · Tetrahedron Letters · 1980 · 59 citations

Photochemical syntheses of 2-aza- and 2-oxabicyclo[2.1.1]hexane ring systems

Yasumitsu Tamura, Hiroyuki Ishibashi, Michio Hirai et al. · The Journal of Organic Chemistry · 1975 · 57 citations

, , +9