Stereoselective Synthesis of a Protected Side Chain of Callipeltin A

Abstract

Matteson homologations of chiral boronic esters proved to be an excellent tool for the synthesis of highly functionalized amino and hydroxy acid residues. This method provides straightforward stereoselective access to the side chain of callipeltin A, a natural marine product with interesting biological activities. Furthermore, this protocol should allow for variations in the substitution pattern in future SAR studies, simply by choosing suitable nucleophiles during the homologation steps.

Stereoselective synthesis of five- and six-membered carbocycles via Matteson homologation/ring closing metathesis

“…In recent years, we have applied the Matteson homologation successfully in several syntheses of natural products, in particular, peptides 18 and peptide/polyketides conjugates. 19 Because of our additional interest in the class of terpenoids, we also investigated methylallylboronic ester 1 , which was converted into the corresponding α-chloro boronic ester 2 under our previously optimised conditions (Scheme 2).…”

1,4-Naphthoquinone Derivative as Efficient Photolabile Molecule: Concise Synthesis and Photorelease of Various Functional Compounds

“…Compound 4 was synthesized by the reaction of 1a with ethyl chloroformate in the presence of pyridine in dichloromethane at room temperature. 11 12 The reaction proceeded smoothly to give 4 in 95% yield. Similarly, the benzyl alcohol derivatives 5a – c were prepared by reacting benzyl chloroformate with 1a – c , respectively.…”

Combining Matteson Homologations and Claisen Rearrangements – An Efficient Protocol for Amino Acid Synthesis

“…[12] Our group's recent involvement in the synthesis of peptide natural products [13] sparked the interest in using the Matteson protocol for the synthesis of highly functionalized and substituted amino acids. [14] Our studies of the Matteson homologation using vinyl nucleophiles (Scheme 1C) [15] motivated us to pursue a different route to form complex amino acid deriva-tives. Vinyl Grignard reagents are well suited to the formation of allylboronic esters (B), which can be converted to chiral allyl alcohols (C).…”