Synthesis of 5α-Androstane-3α,16α,17β-triol from 3β-hydroxy-5-androsten-17-one

Newaz, S. N.; Tcholakian, Robert K.

doi:10.1016/0039-128x(84)90018-7

Cited by 7 publications

(2 citation statements)

References 12 publications

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“…The title compound was obtained as an intermediate during our ongoing investigation of the synthesis of rocuronium bromide; for further information on rocuronium bromide, see: Tuba et al (2002); Auer (2007). For the synthesis, see: Tuba (1980); Newaz & Tcholakian (1984).…”

Section: Related Literaturementioning

confidence: 99%

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10,13-Dimethyl-16-oxo-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl acetate

Shi

Zhang²,

Huang

2010

Acta Cryst E

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Key indicators: single-crystal X-ray study; T = 293 K; mean (C-C) = 0.010 Å; R factor = 0.053; wR factor = 0.136; data-to-parameter ratio = 8.1.In the title compound, C 21 H 30 O 3 , the five-membered ring adopts an envelope conformation, the cyclohexene ring displays a half-chair conformation and the two cyclohexane rings have normal chair conformations. In the crystal structure, weak intermolecular C-HÁ Á ÁO hydrogen bonding links the molecules into supramolecular chains running along [100]. Related literatureRocuronium is a non-depolarizing neuromuscular blocking agent. The title compound was obtained as an intermediate during our ongoing investigation of the synthesis of rocuronium bromide; for further information on rocuronium bromide, see: Tuba et al. Data collectionBruker SMART CCD area-detector diffractometer 5527 measured reflections 1794 independent reflections 864 reflections with I > 2(I) R int = 0.102

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Section: Related Literaturementioning

confidence: 99%

“…The title compound was synthesized according to the procedure reported by Tuba et al (1980) and by Newaz & Tcholakian (1984). Single crystals were obtained from a mixture of ethyl acetate and petroleum ether by slow evaporation at room temperature.…”

Section: S2 Experimentalmentioning

confidence: 99%

10,13-Dimethyl-16-oxo-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl acetate

Shi

Zhang²,

Huang

2010

Acta Cryst E

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Efficient Stereocontrolled Access to 15- and 16-Hydroxy Steroids

Izzo¹,

Filippo²,

Napolitano³

et al. 1999

Eur. J. Org. Chem.

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Four epimeric 15‐ and 16‐hydroxy steroids have been stereoselectively synthesized from epi‐androsterone. The key intermediate is the 3β‐[(tert‐butyldimethylsilyl)oxy]‐5α‐23,24‐bisnorchol‐16‐en‐22‐ol (10), which allows both efficient D‐ring functionalization and the possibility of facile side‐chain construction. In the course of this synthesis, we have found that the stereochemical outcome of the C‐15 carbonyl reduction is strongly dependent on the C‐16 and C‐17 hybridization.

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TheMitsunobu Reaction

1992

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Alkyl and aryl phosphites and phosphines react with compounds having weak heteroatom–heteroatom bonds, such as SS, OO, etc., and with azo compounds to form reactive phosphonium salts. These phosphonium salts in turn promote “redox” condensation reactions with compounds having active hydrogens. The condensation reaction of alcohols using the redox couple of a triaryl‐ or trialkylphosphine and a dialkyl azodicarboxylate has become known as the Mitsunobu reaction, based on his pioneering work in the late 1960s. The overall reaction is summarized, wherein the alcohol (R 1 OH) and acidic compound (H–Nu) are condensed to form product (R 1 –Nu), while triphenylphosphine is oxidized to triphenylphosphine oxide and the azodicarboxylate is reduced to the hydrazine. Although the typical redox combination is diethyl azodicarboxylate (DEAD) and triphenylphosphine, many other combinations have found selected use. The reaction is generally limited to primary and secondary alcohols, although tertiary alcohols react in a few intramolecular and intermolecular reactions. For secondary alcohols the reaction usually proceeds with clean inversion of stereochemistry. The acidic component of the reaction generally has an aqueous p K a < 15, with intramolecular reactions providing the exceptions. Examples of H–Nu include oxygen nucleophiles such as carboxylic acids and phenols; nitrogen nucleophiles such as imides, hydroxamates, and heterocycles; sulfur nucleophiles such as thiols and thioamides; and carbon nucleophiles such as β‐ketoesters. Major reviews of the Mitsunobu reaction were published in 1981 by Mitsunobu and in 1983 by Castro. The former review concentrated on reactions using DEAD/triphenylphosphine, while the latter review focused on reactions in which halogens replaced the hydroxy group using reagents such as triphenylphosphine/carbon tetrachloride, triphenyl phosphite/iodomethane, and triphenylphosphine/ N ‐halosuccinimide. Reactions involving the DEAD/triphenylphosphine redox system are the principal subject of this chapter, with emphasis on the literature between 1981 and 1988.

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Synthesis of 5α-Androstane-3α,16α,17β-triol from 3β-hydroxy-5-androsten-17-one

Cited by 7 publications

References 12 publications

10,13-Dimethyl-16-oxo-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl acetate

10,13-Dimethyl-16-oxo-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl acetate

Efficient Stereocontrolled Access to 15- and 16-Hydroxy Steroids

TheMitsunobu Reaction

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