Total Synthesis of (+/-)-Multifidene, the Gamete Attractant of the Phaeophyte Cutleria multifida

Article abstract of DOI:10.1021/jo00334a034

A short, stereoselective total synthesis of racemic multifidene has been achieved.The key elements of the synthetic scheme are (i) oxyanionic Cope rearrangement of cis³-2,4,7-cyclononatrienol and in situ trapping of the resulting enolate with chlorotrimethylsilane, (ii) stereocontrolled introduction of a phenylseleno group α to the aldehyde functionality, (iii) addition of an ethyl fragment under conditions where the polar PhSe substituent can induce high levels of stereoselection, and (iv) a double inversion sequence to introduce a cis double bond cleanly.