A radical cascade approach to the skeleton of α−Cyclopiazonic Acid

Craft, Russell S (2012) A radical cascade approach to the skeleton of α−Cyclopiazonic Acid. Doctoral thesis (DPhil), University of Sussex.

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Abstract

3-Nitrophthalic acid 2.04 was transformed into 2.10 in 38% yield. Vinylglycine
derivative was synthesised from D-Methionine 2.12 in 42% yield.

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Compounds 2.10 and 2.16 were coupled using Grubbs’ 2nd generation catalyst
creating 2.25. Unfortunately attempts to oxidise the benzylic position were
unsuccessful.

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An alternative approach was investigated using diene 2.40 derived from a precursor to
2.10 and allyl bromide 2.35. Attempts to displace bromide under anionic conditions
were futile. The use of palladium formed conjugated dieneamine 2.65.

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Deprotection, oxidation and elaboration of 2.10 prior to cross metathesis allowed the
synthesis of 2.114, which when subjected to radical conditions, formed a
diastereomeric mixture of 2.220.

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Item Type: Thesis (Doctoral)
Schools and Departments: School of Life Sciences > Chemistry
Subjects: Q Science > QD Chemistry > QD0241 Organic chemistry
Depositing User: Library Cataloguing
Date Deposited: 05 Jul 2012 15:04
Last Modified: 04 Sep 2015 14:12
URI: http://sro.sussex.ac.uk/id/eprint/39782

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