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

Mahadevegowda, S H and Khan, Faiz Ahmed (2014) Total syntheses of (±)-cis- and (±)-trans-neocnidilides. Tetrahedron Letters, 55 (31). pp. 4400-4403. ISSN 0040-4039

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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.

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IITH Creators:
IITH CreatorsORCiD
Item Type: Article
Uncontrolled Keywords: Antimicrobial; Bis-oxidative cleavage; Grob-type fragmentation; Phthalides; Total synthesis
Subjects: Chemistry
Divisions: Department of Chemistry
Depositing User: Team Library
Date Deposited: 02 Dec 2014 07:29
Last Modified: 21 Sep 2017 06:57
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