Synthetic and Mechanistic Studies of
the Retro-Claisen Rearrangement 4. An
Application to the Total Synthesis of
(+)-Laurenyne

Boeckman,, Robert K.; Zhang, Jing; Reeder, Michael R.

doi:10.1021/ol0267174.s001

ol0267174_si_001.pdf (3.24 MB)

Synthetic and Mechanistic Studies of the Retro-Claisen Rearrangement 4. An Application to the Total Synthesis of (+)-Laurenyne

journal contribution

posted on 2002-09-27, 00:00 authored by Robert K. Boeckman,, Jing Zhang, Michael R. Reeder

A novel asymmetric total synthesis of marine natural product (+)-Laurenyne has been achieved. The key elements of the strategy are the sequential metal ion-templated S_N2‘ cyclization affording a highly functionalized chiral vinyl cyclobutane and a retro-Claisen rearrangement for the construction of an eight-membered ring ether.