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Synthesis of the β-hydroxydopa-γ-hydroxy-δ-sulfinylnorvaline component of ustiloxins A and B

Date

Authors

Hunter, Luke

McLeod, Malcolm

Hutton, Craig A

Publisher

Royal Society of Chemistry

Abstract

The dopa-sulfinylnorvaline component of ustiloxins A and B has been prepared using an Evans salen-Al-catalysed aldol reaction with a 6-mercaptoisovanillin derivative, followed by incorporation of the norvaline group and asymmetric oxidation of the resulting sulfide to give the corresponding sulfoxide.

Keywords

Keywords: Alcohols; Alkylation; Aluminum compounds; Catalysis; Chemical modification; Isomers; Oxidation; Reaction kinetics; Sulfur compounds; Synthesis (chemical); Antimitotic agents; Steroselectivity; Sulfinylinorvaline synthesis; Sulfoxides; Aromatic compounds;

URI

http://hdl.handle.net/1885/53057

Collections

ANU Research Publications

Source

Organic and Biomolecular Chemistry

Type

Journal article

DOI

10.1039/b418876d

Restricted until

2037-12-31

Downloads

File

Description

01_Hunter_Synthesis_of_the_2005.pdf (143.86 KB)