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Photochemistry of latifolin and some related compounds

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
42
Issue
17
Identifiers
DOI: 10.1016/s0040-4020(01)82062-7

Abstract

Abstract Latifolin ( 1 ),the major constituent of D.latifolia gave trans 1 -(2,4-dimethoxy-3-hydroxyphenyl)-2-(2-hydroxyphenyl) cyclopropane as the sole photo di-Π-methane rarrangement product. In contrast, its simpler analogues, 3-(2,4,5-trimethoxyphenyl) -3-phenyl prop-1-ene( 3 ) and 3-(2,4-dimethoxyphenyl) -3-phenyl prop-1-ene( 4 ),gave 1:1 mixture of cis and trans cyclopropanes. Dye-sensitized photooxidation of latifolin( 1 ) and dihydrolatifolin ( 16 ) gave novel xanthan derivatives( l5 ) and ( 17 ) involving a crucial step of photooxidative demethylation followed by cyclisation. Similar reaction of the closely related propane 19 gave, interestingly the benzofuran 20 .The propene 22 . lacking free hydroxyl or double bond, gave only the quinone 23 indicating that quinones are intermediates in the above oxidations. The allyl alcohol 24 . having similar feature, undergoes oxidation to the corresponding aldehyde 26 and the benzophenone 28 but not to a quinone.

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