Journal article icon

Journal article

A practical and scaleable total synthesis of the jaborandi alkaloid (+)-pilocarpine

Abstract:

The total synthesis of (+)-pilocarpine (as its nitrate salt) has been achieved in nine steps and 30% overall yield starting from racemic 2-(2′,2′-dimethoxyethyl)propane-1,3-diol, which was desymmetrised via an enzymatic protocol. A high yielding synthesis of a key α-ethylidene lactone precursor has been developed, which involves the palladium-catalysed decarboxylation/carbonylation of a 1,3-dioxan-2-one for formation of the γ-butyrolactone ring. Subsequent hydrogenation of the α-ethylidene la...

Expand abstract
Publication status:
Published

Actions


Access Document


Publisher copy:
10.1016/j.tet.2009.07.010

Authors


More by this author
Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
Journal:
TETRAHEDRON
Volume:
65
Issue:
39
Pages:
8283-8296
Publication date:
2009-09-26
DOI:
ISSN:
0040-4020
URN:
uuid:01aa91c4-a302-4ee1-90e3-17c995778286
Source identifiers:
110647
Local pid:
pubs:110647

Terms of use


Metrics


Views and Downloads






If you are the owner of this record, you can report an update to it here: Report update to this record

TO TOP