Work

Practical Synthesis of 3β-Amino-5-cholestene and Related 3β-Halides Involving i-Steroid and Retro-i-Steroid Rearrangements

Year: 2008

Type: article

Abstract: Derivatives of 3beta-amino-5-cholestene (3beta-cholesterylamine) are of substantial interest as cellular probes and have potential medicinal applications. However, existing syntheses of 3beta-amino-5-cholestene are of limited preparative utility. We report here a practical method for the stereoselective preparation of 3beta-amino-5-cholestene, 3beta-chloro-5-cholestene, 3beta-bromo-5-cholestene, and 3beta-iodo-5-cholestene from inexpensive cholesterol. A sequential i-steroid/retro-i-steroid rearrangement promoted by boron trifluoride etherate and trimethylsilyl azide converted cholest-5-en-3beta-ol methanesulfonate to 3beta-azido-cholest-5-ene with retention of configuration in 93% yield.

Source: Organic Letters

DOI: 10.1021/ol802343z

Authors: Qi Sun, Sutang Cai, Blake R. Peterson

Institutions: Pennsylvania State University, University of Kansas

Language: English

Topic: Steroid Chemistry and Biochemistry

Subfield: Molecular Biology

Field: Biochemistry, Genetics and Molecular Biology

Domain: Life Sciences

Open Access status: green

Funder: National Cancer Institute

Awards: G1458591447, Synthetic Cell Surface Receptors for Anticancer Drug Delivery