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Total synthesis of cis-sylvaticin and synthetic studies towards the synthesis of adjacent THF-THF and THF-THP Annonaceous acetogenins

Total synthesis of cis-sylvaticin and synthetic studies towards the synthesis of adjacent THF-THF and THF-THP Annonaceous acetogenins
Total synthesis of cis-sylvaticin and synthetic studies towards the synthesis of adjacent THF-THF and THF-THP Annonaceous acetogenins
The total synthesis of potent antitumour agent cis-sylvaticin (1.100) has been
completed. Notable steps included the alcoholytic kinetic resolution of epoxide
2.2, two permanganate promoted oxidative cyclisation reactions, a tethered
RCM to unite the two major fragments and the use of P4 phoshazene base to
install the butenolide precursor.

Synthesis of adjacent THP-THF and bis-THF cores via cascade oxidative
cyclisation reactions with permanganate is an attractive route to many
Annonaceous acetogenins. Attempted synthesis of an adjacent THP-THF
core and synthesis of an adjacent bis-THF core are discussed.
Spurr, Ian Bruce
47c5d0a4-3d4c-428f-8e21-8caa1db265ca
Spurr, Ian Bruce
47c5d0a4-3d4c-428f-8e21-8caa1db265ca
Brown, Richard C.D.
21ce697a-7c3a-480e-919f-429a3d8550f5

Spurr, Ian Bruce (2010) Total synthesis of cis-sylvaticin and synthetic studies towards the synthesis of adjacent THF-THF and THF-THP Annonaceous acetogenins. University of Southampton, School of Chemistry, Doctoral Thesis, 174pp.

Record type: Thesis (Doctoral)

Abstract

The total synthesis of potent antitumour agent cis-sylvaticin (1.100) has been
completed. Notable steps included the alcoholytic kinetic resolution of epoxide
2.2, two permanganate promoted oxidative cyclisation reactions, a tethered
RCM to unite the two major fragments and the use of P4 phoshazene base to
install the butenolide precursor.

Synthesis of adjacent THP-THF and bis-THF cores via cascade oxidative
cyclisation reactions with permanganate is an attractive route to many
Annonaceous acetogenins. Attempted synthesis of an adjacent THP-THF
core and synthesis of an adjacent bis-THF core are discussed.

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More information

Published date: June 2010
Additional Information: Part 1: Total synthesis of cis-sylvaticin. Part 2: Synthetic studies towards adjacent THP-THF and bis-THF annonaceous acetogenins
Organisations: University of Southampton

Identifiers

Local EPrints ID: 173853
URI: http://eprints.soton.ac.uk/id/eprint/173853
PURE UUID: a926fc94-8d13-40e8-9fb3-0640acfc7335
ORCID for Richard C.D. Brown: ORCID iD orcid.org/0000-0003-0156-7087

Catalogue record

Date deposited: 16 Feb 2011 16:30
Last modified: 30 Jan 2020 01:28

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