The synthesis of functionalized 13,14-seco-steroids via Grob fragmentation

Steroids
Vladimir A KhripachAede de Groot

Abstract

A synthetic methodology for the synthesis of 13,14-seco-steroids with substituents at C-14 and C-17 is described. The approach involves Grob fragmentation of 14beta-hydroxy-17beta-tosylates, hydroboration-oxidation of the intermediate delta13(17)-olefin, and hydride reduction of the 14-ketone. An unambiguous structural assignment of (13R,14S,17S)-14,17-diacetoxy-3-methoxy-7alpha-methyl-13,14-secoestra-1,3,5(10)-triene was determined by X-ray analysis.

References

Jan 1, 1976·Journal of the Chemical Society. Perkin Transactions 1·I KirsonE Glotter
Jan 1, 1990·Phytochemistry·J D ThackerC Bumgardner
Jul 1, 1973·Steroids·G H Rasmusson, G E Arth
Jul 1, 1973·Steroids·A Segaloff, R B Gabbard
Jan 1, 1970·Journal of the Chemical Society. Perkin Transactions 1·T MatsuuraY Butsugan
Aug 1, 1965·The Journal of Organic Chemistry·M TANABE, D F CROWE
Jul 13, 2004·Steroids·Vladimir A KhripachAede de Groot

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Citations

Mar 31, 2012·Chemistry : a European Journal·Filip HesslerMartin Kotora
Sep 24, 2015·The Journal of Organic Chemistry·Robert J Sharpe, Jeffrey S Johnson
Mar 23, 2006·Steroids·Vladimir A KhripachAede de Groot
Apr 10, 2015·Journal of the American Chemical Society·Robert J Sharpe, Jeffrey S Johnson
Feb 3, 2006·Natural Product Reports·James R Hanson
Nov 22, 2013·Organic & Biomolecular Chemistry·Qingliang YangPradipta Das
Feb 19, 2010·Chemical Reviews·Kathrin Prantz, Johann Mulzer

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