Practical synthesis of 3beta-amino-5-cholestene and related 3beta-halides involving i-steroid and retro-i-steroid rearrangements.

Organic Letters
Qi SunBlake R Peterson

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.

References

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Citations

Dec 2, 2011·Langmuir : the ACS Journal of Surfaces and Colloids·Max LönnforsJ Peter Slotte
Feb 4, 2014·Steroids·Aneta M TomkielJacek W Morzycki
Oct 12, 2016·ACS Central Science·Jian YangAlexander Kros
Nov 7, 2015·Tetrahedron Letters·Ryan A DavisJacquelyn Gervay-Hague
Aug 20, 2015·Chemical Communications : Chem Comm·David HymelBlake R Peterson
Mar 23, 2017·Chemical Communications : Chem Comm·Takuya SagamiSatoshi Shinoda
Sep 2, 2011·Chemistry : a European Journal·Henri A van KalkerenFloris L van Delft
Aug 12, 2014·Chemistry : a European Journal·Jonathan P Moerdyk, Christopher W Bielawski
Dec 15, 2015·Beilstein Journal of Organic Chemistry·Mohamed Ramadan El Sayed AlyShams Hashim Abdel-Hafez
May 12, 2016·Chembiochem : a European Journal of Chemical Biology·Nicolai Stuhr-HansenOla Blixt
Oct 6, 2017·Langmuir : the ACS Journal of Surfaces and Colloids·Geert A DaudeyAimee L Boyle
Feb 21, 2018·ACS Applied Materials & Interfaces·Stéphane IsabettiniSimon Kuster
Apr 18, 2017·The Journal of Organic Chemistry·Xiaodong ZouHongjian Lu
Jul 13, 2011·The Journal of Organic Chemistry·Ross M DentonAndrew M Poulton

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