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Simple synthesis of diplodialides from a butadiene telomer

โœ Scribed by Jiro Tsuji; Tadakatsu Mandai

Publisher
Elsevier Science
Year
1978
Tongue
French
Weight
201 KB
Volume
19
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

A (;I and B (z), naturally occurring ten-membered lactones which were isolated from the culture filtrate,of Diplodia pinea by Ishida and Wada' and show unique biological activity. A butadiene telomer 3 easily available by palladium catalyzed reaction is a starting material and the method is based on the two carbon elongation and lactone formation using modified intramolecular Reformatsky reaction. In our continuous effort to apply palladium catalyzed reactions to simple syntheses of natural products, we have synthesized a number of natural products such as civetone 2 and recifeiolide. 3 In the present synthesis of diplodialides, two important palladium catalyzed reactions, namely oxidation of terminal olefins to methyl ketones and telomerization of butadiene, were utilized. 8-Acetoxy-1,6-octadiene (_3), which is easily prepared by the palladium catalyzed telomerization of butadiene with acetic acid, 4 is the starting material. As shown in scheme I, comparison of the structures of 1 and 2 with that of 3 clearly indicates that the functionality of 3 is very suitable for the construction of the unsaturated lactone skeleton. The double bona at C6 in 3 has the required trans configuration and is located at the right position.

Also there exists the appropriate oxygen function.

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