Total syntheses of (±)-cis- and (±)-trans-neocnidilides.

Authors :: Mahadevegowda, Surendra H.
Khan, Faiz Ahmed
Source :: Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry. Jul2014, Vol. 55 Issue 31, p4400-4403. 4p.
Publication Year :: 2014
Abstract: Total syntheses of two antimicrobial natural products (±)-cis-neocnidilide and (±)-trans-neocnidilide starting from a readily preparable cyclohexa[b]-fused 5-oxabicyclo[2.1.1]hexane derivative are presented. The diastereomeric tetrahydrofuran tricarboxylate epimers obtained from a BF3⋅OEt2 promoted Grob-type fragmentation of the oxa-bicycle derivative were converted into title natural products by employing pyridinium dichromate/acetic anhydride mediated bis-oxidative cleavage reaction. [ABSTRACT FROM AUTHOR]

Subjects :: *CHEMICAL synthesis
*ANTI-infective agents
*NATURAL products
*HEXANE
*CHEMICAL derivatives
*TETRAHYDROFURAN

Language :: English
ISSN :: 00404039
Volume :: 55
Issue :: 31
Database :: Academic Search Index
Journal :: Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry
Publication Type :: Academic Journal
Accession number :: 97002129
Full Text :: https://doi.org/10.1016/j.tetlet.2014.06.007