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1.
Beilstein J Org Chem ; 13: 2326-2331, 2017.
Article in English | MEDLINE | ID: mdl-29181112

ABSTRACT

Herein, we present a new strategy for the preparation of a broad range of brassinosteroid biosynthetic precursors/metabolites differing by the ring A fragment. The protocol is based on the use of readily available phytohormones of this class bearing a 2α,3α-diol moiety (epibrassinolide or epicastasterone) as starting materials. The required functionalities (Δ2-, 2α,3α- and 2ß,3ß-epoxy-, 2α,3ß-, 2ß,3α-, and 2ß,3ß-dihydroxy-, 3-keto-, 3α- and 3ß-hydroxy-, 2α-hydroxy-3-keto-) were synthesized from 2α,3α-diols in a few simple steps (Corey-Winter reaction, epoxidation, oxidation, hydride reduction, etc.).

2.
Steroids ; 102: 53-9, 2015 Oct.
Article in English | MEDLINE | ID: mdl-26210210

ABSTRACT

Three BS-BODIPY (brassinosteroids-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene) conjugates were synthesized and their fluorescent and immunological properties were investigated. Two of the conjugates, having present all the functional groups characteristic of BS, were shown to be potentially useful as biological probes to study involvement of BS into physiological processes in living cells.


Subject(s)
Boron Compounds/chemistry , Brassinosteroids/chemistry
3.
Steroids ; 97: 72-7, 2015 May.
Article in English | MEDLINE | ID: mdl-25194458

ABSTRACT

A new route to the synthesis of minor brassinosteroids with a cholestane framework (28-norcastasterone and 28-norbrassinolide) has been proposed. It makes use of commercially available 24-epicastasterone as a starting material. In addition, [26,26,26-(2)H3]-28-norcastasterone and [26,26,26-(2)H3]-28-norbrassinolide have been prepared as tools for analytical applications. The key steps were regioselective manipulations of functional groups in 24-epicastasterone, oxidative cleavage of 22,23-diol group and Claisen rearrangement.


Subject(s)
Brassinosteroids/chemical synthesis , Cholestanes/chemistry , Brassinosteroids/chemistry , Molecular Conformation , Stereoisomerism
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