Abstract: 1,6-Enynes are important intermediates in organic synthesis and they are not easy to make, especially those connected with a neopentylchain. Here we describe a simple, general method to make 1,6-enynes in three steps from commercially available materials. The sequence includes a tandem fragmentation/olefination of vinylogous alcohol triflate 1  . The utility of this new tandem reaction was demonstrated by setting it as a divergent starting point to synthesize alcyopterosinA, hirsutene, and illudol, with application to other sesquiterpenes planned.

Tandem fragmentation/olefination yielding high-value 1,6-Enynes and applications in syntheses of natural products

244th National Meeting (2012)

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