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Title: Total synthesis of cis-sylvaticin and synthetic studies towards the synthesis of adjacent THF-THF and THF-THP Annonaceous acetogenins
Author: Spurr, Ian Bruce
ISNI:       0000 0004 2695 4566
Awarding Body: University of Southampton
Current Institution: University of Southampton
Date of Award: 2010
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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.
Supervisor: Brown, Richard Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: QD Chemistry