title: Total synthesis of Spiruchostatin A via chemoselective macrocyclization using an accessible enantiomerically pure latent thioester.
abstract: HDAC inhibitor Spiruchostatin A was synthesized via a route that differs significantly from previously reported routes. The key step involves a latent thioester that initiates a chemoselective transformation similar to native chemical ligation to form the macrocyclic alanine-cysteine amide bond. The easily prepared latent thioester--the first such moiety reported in enantiomerically pure form--is designed with a pendant carboxylic acid to serve as a solid-phase linker for the synthesis of cyclic, cysteine-containing, peptidic materials.
authors.affiliation: Department of Chemistry, Hobart College, Geneva, New York 14456, USA.
authors.forename: Nicole A
authors.initials: NA
authors.lastname: Calandra
authors.forename: Yim Ling
authors.initials: YL
authors.lastname: Cheng
authors.forename: Kimberly A
authors.initials: KA
authors.lastname: Kocak
authors.forename: Justin S
authors.initials: JS
authors.lastname: Miller