Vinyl cyclobutanol strategy for halogenated cyclopentanoids

Total Synthesis of seco-Plakortolide E and (−)-ent-Plakortolide I: Absolute Configurational Revision of Natural Plakortolide I

“…Conversely to literature precedents, no reaction occurred . Consequently, we adopted a stepwise method which consisted of selective deprotection of the primary TES ether with silica gel followed by Swern oxidation to provide aldehyde 6 in 60% over three steps from 13 . With 6 in hand, the stage was set up for the Mukaiyama aldol addition.…”

Synthesis of β-, γ-, δ-, ..., ω-Halogenated Ketones and Aldehydes

“…Likewise, Fukumoto and co-workers developed an iodonium ion-mediated ring-expansion of olefinic cyclobutanols 416 with I 2 /NaHCO 3 or NIS (Scheme ) . All investigated reactions furnished neopentyl-type β-iodinated cyclopentanones 417 and 418 in moderate to high yields.…”

The Application of Cyclobutane Derivatives in Organic Synthesis

“…Thus, exposure of 135 to a catalytic quantity of iodine in PhH at room temperature for 16 h was sufficient to induce its efficient conversion to 136 in 91% yield, a key step in the total synthesis of (±)-hirsutene 52 A new strategy for the synthesis of iodoalkylated cyclopentanoids was also based on the iodonium ion mediated ring expansion of olefinic cyclobutanols. For example, after treatment of iodine or N-iodosuccinimide in the presence of NaHCO 3 in Et 2 O at 0 • C, cyclobutanol 137 was converted to 138 and 139 53 .…”