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<br/>completed. Notable steps included the alcoholytic kinetic resolution of epoxide<br/>2.2, two permanganate promoted oxidative cyclisation reactions, a tethered<br/>RCM to unite the two major fragments and the use of P4 phoshazene base to<br/>install the butenolide precursor.<br/><br/>Synthesis of adjacent THP-THF and bis-THF cores via cascade oxidative<br/>cyclisation reactions with permanganate is an attractive route to many<br/>Annonaceous acetogenins. Attempted synthesis of an adjacent THP-THF<br/>core and synthesis of an adjacent bis-THF core are discussed.

Name dc:type.qualificationname

Ph.D.

Level dc:type.qualificationlevel

doctoral

Grantor dc:publisher.institution

University of Southampton

Year dc:date.issued

2010

Author dc:creator

• Spurr, Ian Bruce

Advisor dc:contributor.advisor

• Brown, Richard C.D.