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Model studies in the taxane diterpene series - Part. I

✍ Scribed by Humberto Cervantes; Duc Do Khac; Marcel Fetizon; Frédéric Guir; Jean-Claude Beloeil; Jean-Yves Lallemand; Thierry Prange

Book ID
104204468
Publisher
Elsevier Science
Year
1986
Tongue
French
Weight
738 KB
Volume
42
Category
Article
ISSN
0040-4020

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✦ Synopsis

Photochemical 12 + 21 cycloaddition of enol acetate c);cTohexene led to a 3 : * to 1 mixture of the tetracyclic photoadducts 4 and B which, through reverse aldol reactions, under mild alkaline condZions produced twu compounds : a tetracyclic ketone l3 and a tricyclic diketone 14 . Hydrolytic cleavage in methanoli~hydrochloric acid of 15 and s-resulting fran irradiation of the enol ether lob to cycloh=ene gave rise to the rearranged tricyclic diketone 14 o= . The trans stereochemistry 3ca, 88 of the fused-ring system in q established by X-ray measuresrents, is different fran the sterhistry of the naturally occuring taxane derivatives . Ejuct &ment.i cmpo'ktX.onen quod v&n habet in taxo baccata, pho.tetoch.&~& bent&&, qu.&fam h exemp& bimp&cio~e k?.d&% expehti bunt . Pticonmwde &en accidit CLt n&tie h quaebtie ,(i.gwta d&b&&% bti ejub nei nazWa puzeb&e

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