Biomimetic Approaches: Synthesis of (±)-Homodimericin A

Abstract

A brief history of biomimetic total synthesis is reviewed. The molecules covered in this SynPact account include tropinone (Robinson, 1917), usnic acid (Barton, 1956), progesterone (Johnson, 1971), endiandric acids (Nicolaou, 1982), methyl homosecodaphniphyllate (Heathcock, 1988), glabrescol (Corey, 2000), FR182877 (Sorensen, 2002 and Evans, 2002), and intricarene (Pattenden, 2006 and Trauner, 2006). Key biomimetic transformations of the syntheses are highlighted. Our recent biomimetic synthesis of homodimericin A is also discussed. Our study validates the key steps of the biosynthesis proposed by Clardy et al.

Recent progress in the electrochemical selenofunctionalization of alkenes and alkynes

“…36 The first method of synthesizing these molecules was reported by Yan through I 2 -mediated thioselenation of alkenes. 37 An electrochemical method for the synthesis of β-selenylethyl dithiocarbamates was recently developed by Dong and Ren et al (Scheme 10). 38 This protocol employed nBu 4 NBF 4 as the supporting electrolyte and K 2 CO 3 as a base in CH 3 CN at ambient temperature.…”

Advances in Difunctionalization of Olefins with Diorganyl Dichalcogenides

“…Soon later, Yan's research group used molecular iodine as a catalyst to prepare β-tryptosyl dithiocarbamates from olefins, diselenides, and sodium dithiocarbamates. [42] The difunctionalization reaction of the olefins has the advantages of mild conditions and simple operations. It obtained β-tryptoyl dithiocarbamates with high regional selectivities and high yields, where the highest yield of 14 examples reached 92 % (Scheme 27).…”