Microwave-Promoted Rearrangement of Hecogenin Derivatives into Cnor- D-homo Steroids

Zhou      Huan; Yue      Pei; Ruan      Hanli; Zhang      Yonghui; Pi      Huifang; Zhang      Peng; Wu      Jizhou

doi:10.2174/157017809787582799

Abstract

By means of microwave irradiation, the rearrangement from 12β-tosylate and 12β-alcohol of hecogenin derivatives into C-nor-D-homo-Δ17a(18)-olefin (2) and the Δ13(17a)-isomer (3) was achieved. With this method, the controlled solvolysis in anhydrous pyridine gave total conversion to desired exocyclic-olefin which is expected to be a building block of isosteroidal alkaloids.

Keywords: Hecogenin derivatives, rearrangement, solvolysis, C-nor-D-homo, isosteroids, microwave irradiation

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Letters in Organic Chemistry

Title: Microwave-Promoted Rearrangement of Hecogenin Derivatives into Cnor- D-homo Steroids

Volume: 6 Issue: 2

Author(s): Zhou Huan, Yue Pei, Ruan Hanli, Zhang Yonghui, Pi Huifang, Zhang Peng and Wu Jizhou

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Keywords: Hecogenin derivatives, rearrangement, solvolysis, C-nor-D-homo, isosteroids, microwave irradiation

Abstract: By means of microwave irradiation, the rearrangement from 12β-tosylate and 12β-alcohol of hecogenin derivatives into C-nor-D-homo-Δ17a(18)-olefin (2) and the Δ13(17a)-isomer (3) was achieved. With this method, the controlled solvolysis in anhydrous pyridine gave total conversion to desired exocyclic-olefin which is expected to be a building block of isosteroidal alkaloids.

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Huan Zhou, Pei Yue, Hanli Ruan, Yonghui Zhang, Huifang Pi, Peng Zhang and Jizhou Wu, Microwave-Promoted Rearrangement of Hecogenin Derivatives into Cnor- D-homo Steroids, Letters in Organic Chemistry 2009; 6 (2) . https://dx.doi.org/10.2174/157017809787582799