Furoventalene is a sesquiterpene natural product that has been previously synthesized by other research groups, but only in low (<10%) overall yield. An improved synthesis has been developed which takes advantage of a different approach to the construction of the benzofuran portion of the molecule, involving a microwave-accelerated Friedel-Crafts reaction. Microwave-accelerated organic synthesis (MAOS) has been demonstrated in many cases to afford considerably shorter reaction times, and higher yields of desired product. Results in this lab have shown considerable improvement in yield of the acylation product compared to traditional thermal methods. Subsequent elaboration of the molecule by Grignard addition followed by dehydration of the resulting alcohol gives a key intermediate, which may be subjected to Kumada coupling to affix the necessary side chain to complete the synthesis. Microwave-accelerated versus traditional Kumada coupling methods will be compared and presented in order to complete the synthesis.

Novel approach to the total synthesis of furoventalene, a sesquiterpene natural product

244th National Meeting (2012)

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