- 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
- Publisher copy:
- 10.1016/j.tet.2009.07.010
-
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- 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
- Language:
- English
- Keywords:
- Copyright date:
- 2009
Journal article
A practical and scaleable total synthesis of the jaborandi alkaloid (+)-pilocarpine
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