78739-42-1Relevant articles and documents
Absolute Configuration of Multifidene as Deduced by Total Synthesis of the Unnatural Levorotatory Enantiomer
Paquette, Leo A.,Coghlan, Michael J.,Hayes, Peter C.
, p. 4516 - 4518 (2007/10/02)
The powerful sperm attractant of the brown alga Cutleria multifida (+)-multifidene (1), is shown to possess the 3S,4S configuration.The protocol, which parallels our earlier synthesis of the racemic polyolefinic hydrocarbon, begins with (-)-cis-(5-vinyl-2
Total Synthesis of (+/-)-Multifidene, the Gamete Attractant of the Phaeophyte Cutleria multifida
Crouse, Gary D.,Paquette, Leo A.
, p. 4272 - 4274 (2007/10/02)
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.
