Synthesis of novel 16-spiro steroids: spiro-7'-(aryl)tetrahydro-1H-pyrrolo[1,2-c][1,3]thiazolo-trans-androsterone hybrid heterocycles

Selvaraj Kanchithalaivan; Raju Ranjith Kumar; Subbu Perumal

doi:10.1016/j.steroids.2012.12.017

Synthesis of novel 16-spiro steroids: spiro-7'-(aryl)tetrahydro-1H-pyrrolo[1,2-c][1,3]thiazolo-trans-androsterone hybrid heterocycles

Steroids. 2013 Apr;78(4):409-17. doi: 10.1016/j.steroids.2012.12.017. Epub 2013 Jan 31.

Authors

Selvaraj Kanchithalaivan¹, Raju Ranjith Kumar, Subbu Perumal

Affiliation

¹ Department of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625 021, Tamil Nadu, India.

PMID: 23376110
DOI: 10.1016/j.steroids.2012.12.017

Abstract

The 1,3-dipolar cycloaddition of azomethine ylide derived in situ from the reaction of acenaphthylene-1,2-dione and 1,3-thiazolane-4-carboxylic acid to various exocyclic dipolarophiles synthesized from trans-androsterone and trans-dehydroandrosterone afforded a library of novel spiro[5'.2″]acenaphthylene-1″-one-spiro[16.6']-(7'-aryl)-tetrahydro-1H-pyrrolo [1,2-c][1,3]thiazolo-trans-androsterone/dehydroandrosterone hybrid heterocycles respectively. These reactions proceeded stereo-specifically affording a single isomer of the 16-spiro steroids in excellent yields.

Publication types

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

MeSH terms

Acenaphthenes / chemical synthesis*
Acenaphthenes / chemistry
Androsterone / analogs & derivatives*
Androsterone / chemical synthesis
Androsterone / chemistry
Heterocyclic Compounds / chemical synthesis*
Heterocyclic Compounds / chemistry
Models, Molecular
Molecular Conformation
Spiro Compounds / chemical synthesis*
Spiro Compounds / chemistry

Substances

Acenaphthenes
Heterocyclic Compounds
Spiro Compounds
Androsterone