α-Alkylidene-γ-butyrolactone synthesis via one-pot C-H insertion/olefination: Substrate scope and the total synthesis of (±)-cedarmycins A and B

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 -