Graduate Thesis Or Dissertation
 

Synthesis of the 2, 3, 3a, 8a-tetrahydro-2-hydroxy-furo [2, 3-b]benzofuran ring system, an aflatoxin moiety

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  • A new method for the preparation of the 2, 3, 3a,8a-tetrahydro-2-hydroxyfuro[2, 3-b] benzofuran, XXX, ring system has been developed. The synthesis envolved a substitution reaction of phenol, XXIV, with 1-bromo-2, 5-hexadiene, XXV, to give 2, 5-hexadien-l -yl phenyl ether, XXVII. The ether was rearranged via an ortho-Claisen rearrangement to 3-(o-hydroxyphenyl)-l, 5-hexadiene, XXVIII. The double bonds of the phenolic diene were cleaved to dialdehyde XXIX which cyclized to the desired product, XXX. The structure of XXX was verified by infrared, ultraviolet, nuclear magnetic resonance, and mass spectral data, as well as by a preparation from an adaptation of a published route.
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