TY - JOUR
T1 - α-Alkylidene-γ-butyrolactone synthesis via one-pot C-H insertion/olefination
T2 - Substrate scope and the total synthesis of (±)-cedarmycins A and B
AU - Lloyd, Matthew G.
AU - D'Acunto, Mariantonietta
AU - Taylor, Richard J K
AU - Unsworth, William P.
PY - 2014/10/7
Y1 - 2014/10/7
N2 - A system for the synthesis of α-alkylidene-γ-butyrolactones via a one-pot C-H insertion/olefination sequence is described. The process is based on the rhodium catalysed C-H insertion reaction of α-diazo-α-(diethoxyphosphoryl)acetates. The mild reaction conditions, operational simplicity and ready availability of starting materials are all key features. A wide range of successful reaction systems are reported (41 examples) highlighting the generality of the method. The application of this method in the total synthesis of the natural products (±)-cedarmycins A and B is also described.
AB - A system for the synthesis of α-alkylidene-γ-butyrolactones via a one-pot C-H insertion/olefination sequence is described. The process is based on the rhodium catalysed C-H insertion reaction of α-diazo-α-(diethoxyphosphoryl)acetates. The mild reaction conditions, operational simplicity and ready availability of starting materials are all key features. A wide range of successful reaction systems are reported (41 examples) highlighting the generality of the method. The application of this method in the total synthesis of the natural products (±)-cedarmycins A and B is also described.
KW - C-H insertion
KW - Cedarmycins A and B
KW - Rhodium carbenoids
KW - Tandem reactions
KW - α-Methylene-γ-butyrolactones
UR - http://www.scopus.com/inward/record.url?scp=84908475856&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2014.09.054
DO - 10.1016/j.tet.2014.09.054
M3 - Article
SN - 0040-4020
VL - 71
SP - 7107
EP - 7123
JO - Tetrahedron
JF - Tetrahedron
IS - 39
ER -