Toward synthesis of carbasugars (+)-gabosine C, (+)-COTC, (+)-pericosine B, and (+)-pericosine C

D Chanti Babu; Ch Bhujanga Rao; K Venkatesham; J Jon Paul Selvam; Y Venkateswarlu

doi:10.1016/j.carres.2013.08.008

Toward synthesis of carbasugars (+)-gabosine C, (+)-COTC, (+)-pericosine B, and (+)-pericosine C

Carbohydr Res. 2014 Mar 31:388:130-7. doi: 10.1016/j.carres.2013.08.008. Epub 2013 Aug 20.

Authors

D Chanti Babu¹, Ch Bhujanga Rao², K Venkatesham², J Jon Paul Selvam², Y Venkateswarlu²

Affiliations

¹ Division of Natural Product Chemistry, Indian Institute of Chemical Technology, Hyderabad 500 007, India. Electronic address: chantibabuiict@gmail.com.
² Division of Natural Product Chemistry, Indian Institute of Chemical Technology, Hyderabad 500 007, India.

PMID: 24637047
DOI: 10.1016/j.carres.2013.08.008

Abstract

Asymmetric total synthesis of (+)-gabosine C, (+)-pericosine B, and (+)-pericosine C has been reported from readily available d-(-)-isoascorbic acid and d-ribose involving Grubbs ring closing metathesis, Morita-Baylis-Hillman (MBH) reaction, and Luche reduction.

Keywords: Carbasugars; Luche reduction d-(−)-isoascorbic acid and d-ribose; Morita–Baylis–Hillman (MBH) reaction; Periconia byssoides; Streptomyces.

Publication types

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

MeSH terms

Ascorbic Acid / chemistry
Carbasugars / chemical synthesis*
Catalysis
Cyclohexanols / chemical synthesis*
Cyclohexanones / chemical synthesis*
Molecular Structure
Oxidation-Reduction
Ribose / chemistry
Shikimic Acid / analogs & derivatives*
Shikimic Acid / chemical synthesis
Stereoisomerism

Substances

Carbasugars
Cyclohexanols
Cyclohexanones
pericosine B
pericosine C
Shikimic Acid
isoascorbic acid
KD 16U1
Ribose
Ascorbic Acid