A Mild One-Pot Method for Conversion
of Various Steroidal Secondary Alcohols into the Corresponding
Olefins

Raju Ranjith Kumar; Shrutisagar Dattatraya Haveli; Henri B. Kagan

doi:10.1055/s-0030-1260803

LETTER

A Mild One-Pot Method for Conversion of Various Steroidal Secondary Alcohols into the Corresponding Olefins

Raju Ranjith Kumar, Shrutisagar Dattatraya Haveli, Henri B. Kagan*
Laboratoire de Catalyse Moléculaire, Institut de Chimie Moléculaire et des Matériaux d’Orsay (UMR CNRS 8182), Bâtiment 420, Université Paris-Sud, 91405 Orsay, France
Fax: +33(1)69154680; e-Mail: henri.kagan@u-psud.fr;

Abstract

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Abstract

The addition of Tf₂O to some hydroxy steroids in the presence of excess base directly leads to steroidal olefins. This methodology is useful for the one-pot synthesis of Δ^²- or Δ^³-steroids under mild conditions from the corresponding alcohols.

Key words

alcohols - biliary acid, elimination - steroids - triflic anhydride

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References

References and Notes

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18

The Tf₂O/DMAP protocol was applied to primary alcohols (aliphatic alcohols, bisacetonide of glucopyranose), which were transformed into the corresponding triflates devoid of elimination products. Triflates were also produced from some secondary alcohols in carbohydrate family (as bisacetonide of galactopyranose). Terpenoid secondary alcohols provided elimination products.