OXIDATIVE DECARBOXYLATION OF PODOCARPIC ACID-DERIVATIVES

Authors
CAMBIE RC DAVY PK MITCHELL LH RICKARD CEF RUTLEDGE PS
Citation
Rc. Cambie et al., OXIDATIVE DECARBOXYLATION OF PODOCARPIC ACID-DERIVATIVES, Australian Journal of Chemistry, 51(8), 1998, pp. 653-660
Citations number
25
Categorie Soggetti
Chemistry
Journal title
Australian Journal of Chemistry → ACNP
ISSN journal
00049425
Volume
51
Issue
8
Year of publication
1998
Pages
653 - 660
Database
ISI
SICI code
0004-9425(1998)51:8<653:ODOPA>2.0.ZU;2-T
Abstract
The radical decarboxylation-sulfoxide cycloelimination of 2'-pyridylth io esters formed from a series of podocarpic acid derivatives gives De lta(4(18))-alkenes in high yield. An exception is the 13-nitro acid (2 ) which affords a thiohydroxamic ester (28), the relative stability of which is attributed to inhibition of the radical chain reaction by th e nitro group. The stereochemistry of the pyridyl sulfide (18) has bee n confirmed by X-ray crystallography.