Synthesis of polyhydroxylated Δ13-17,17-dialkyl-18- norsteroids by BF3·Et2O/Ac2O-promoted Wagner-Meerwein rearrangement of furostanols

Martín A. Iglesias-Arteaga; José M. Mendez-Stivalet; Nury Pérez

doi:10.1177/1934578x0700200109

Synthesis of polyhydroxylated Δ¹³-17,17-dialkyl-18- norsteroids by BF₃·Et₂O/Ac₂O-promoted Wagner-Meerwein rearrangement of furostanols

Martín A. Iglesias-Arteaga, José M. Mendez-Stivalet, Nury Pérez

Research output: Contribution to journal › Article › peer-review

2 Scopus citations

Abstract

Two polyhydroxylated Δ¹³-17,17-dialkyl-18-norsteroids were prepared by BF₃·Et₂O/Ac₂O-promoted regioselective E-ring cleavage/ 1-2 hydride shift/ Wagner-Meerwein rearrangement of furostanols derived from the steroid sapogenins diosgenin and sarsasapogenin. Details of the spectroscopic characterization are discussed. (Grapg Presented).

Original language	English
Pages (from-to)	47-50
Number of pages	4
Journal	Natural Product Communications
Volume	2
Issue number	1
DOIs	https://doi.org/10.1177/1934578x0700200109
State	Published - 2007
Externally published	Yes

Keywords

1-2 hydride shift
Furostanols
NMR
Tetrahydrofuran cleavage
Wagner-Meerwein rearrangement

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10.1177/1934578x0700200109

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title = "Synthesis of polyhydroxylated Δ13-17,17-dialkyl-18- norsteroids by BF3·Et2O/Ac2O-promoted Wagner-Meerwein rearrangement of furostanols",

abstract = "Two polyhydroxylated Δ13-17,17-dialkyl-18-norsteroids were prepared by BF3·Et2O/Ac2O-promoted regioselective E-ring cleavage/ 1-2 hydride shift/ Wagner-Meerwein rearrangement of furostanols derived from the steroid sapogenins diosgenin and sarsasapogenin. Details of the spectroscopic characterization are discussed. (Grapg Presented).",

keywords = "1-2 hydride shift, Furostanols, NMR, Tetrahydrofuran cleavage, Wagner-Meerwein rearrangement",

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AU - Iglesias-Arteaga, Martín A.

AU - Mendez-Stivalet, José M.

AU - Pérez, Nury

PY - 2007

Y1 - 2007

N2 - Two polyhydroxylated Δ13-17,17-dialkyl-18-norsteroids were prepared by BF3·Et2O/Ac2O-promoted regioselective E-ring cleavage/ 1-2 hydride shift/ Wagner-Meerwein rearrangement of furostanols derived from the steroid sapogenins diosgenin and sarsasapogenin. Details of the spectroscopic characterization are discussed. (Grapg Presented).

AB - Two polyhydroxylated Δ13-17,17-dialkyl-18-norsteroids were prepared by BF3·Et2O/Ac2O-promoted regioselective E-ring cleavage/ 1-2 hydride shift/ Wagner-Meerwein rearrangement of furostanols derived from the steroid sapogenins diosgenin and sarsasapogenin. Details of the spectroscopic characterization are discussed. (Grapg Presented).

KW - 1-2 hydride shift

KW - Furostanols

KW - NMR

KW - Tetrahydrofuran cleavage

KW - Wagner-Meerwein rearrangement

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VL - 2

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EP - 50

JO - Natural Product Communications

JF - Natural Product Communications

IS - 1

ER -

Synthesis of polyhydroxylated Δ¹³-17,17-dialkyl-18- norsteroids by BF₃·Et₂O/Ac₂O-promoted Wagner-Meerwein rearrangement of furostanols

Abstract

Keywords

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