Chemoenzymatic synthesis of carbasugars (+)-pericosines A-C from diverse aromatic cis-dihydrodiol precursors

Derek R Boyd; Narain D Sharma; Carmen A Acaru; John F Malone; Colin R O'Dowd; Christopher C R Allen; Paul J Stevenson

doi:10.1021/ol100525r

Chemoenzymatic synthesis of carbasugars (+)-pericosines A-C from diverse aromatic cis-dihydrodiol precursors

Org Lett. 2010 May 21;12(10):2206-9. doi: 10.1021/ol100525r.

Authors

Derek R Boyd¹, Narain D Sharma, Carmen A Acaru, John F Malone, Colin R O'Dowd, Christopher C R Allen, Paul J Stevenson

Affiliation

¹ School of Chemistry and Chemical Engineering, Queen's University of Belfast, Belfast BT9 5AG, United Kingdom.

PMID: 20411952
DOI: 10.1021/ol100525r

Abstract

cis-Dihydrocatechols, derived from biological cis-dihydroxylation of methyl benzoate, iodobenzene and benzonitrile, using the microorganism Pseudomonas putida UV4, were converted into pericosines A, C, and B, respectively. This approach constitutes the shortest syntheses, to date, of these important natural products with densely packed functionalities.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Molecular Conformation
Naphthalenes / chemistry*
Shikimic Acid / analogs & derivatives*
Shikimic Acid / chemical synthesis
Shikimic Acid / chemistry
Stereoisomerism

Substances

Naphthalenes
methyl (3S,4S,5S,6S)-6-chloro-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate
pericosine B
pericosine C
trans-1,2-dihydro-1,2-naphthalenediol
Shikimic Acid