Formal total syntheses of (+)-prelaureatin and (+)-laurallene by diastereoselective brook rearrangement-mediated [3 + 4] annulation.
The formal syntheses of (+)-prelaureatin (1) and (+)-laurallene (2), halogenated eight-membered-ring ethers, are described. The key step of our strategy relies on diastereoselective construction of a trans-alpha,alpha'-disubstituted oxocene structure through a Brook rearrangement-mediated [3 + 4] annulation with acryloylsilane 9 and 6-oxa-2-cycloheptenone derivative 22'.
Sasaki
Michiko
M
Department of Synthetic Organic Chemistry, Graduate School of Medical Sciences, Hiroshima University, 1-2-3 Kasumi, Minami-Ku, Hiroshima 734-8553, Japan.
Oyamada
Kazuhisa
K
Takeda
Kei
K
D000466:Alkadienes / Q000138:chemical synthesis*; D004987:Ethers / Q000138:chemical synthesis*; D054879:Halogenation; D035964:Oxocins / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000466:Alkadienes; D004987:Ethers; D035964:Oxocins; C551786:laurallene; C551785:prelaureatin; C025947:propadiene