15β-hydroxysteroids (part iii). * steroids of the human perinatal period: The synthesis of 3β, 15β, 17α-trihydroxy-5-pregnen-20-one. Application of n-butyl boronic acid protection of a 17,20-glycol

Steroids

Volumn 61, Issue 1, 1996, Pages 11-17

  Joannou, George E ^a,b   Reeder, Anthony Y ^a  

^a ROYAL PRINCE ALFRED HOSPITAL   (Australia)

^b CHILDREN S HOSPITAL AT WESTMEAD   (Australia)

Author keywords

15 hydroxysteroids; Adrenal; Hyperplasia; N butyl boronate; Neonate; Synthesis

Indexed keywords

3BETA,15BETA,17ALPHA TRIHYDROXYPREGN 5 EN 20 ONE; ACETIC ANHYDRIDE; ALKENE; BORONIC ACID DERIVATIVE; HYDROGEN PEROXIDE; HYDROXYSTEROID; LITHIUM; N BROMOSUCCINIMIDE; SODIUM HYDROXIDE; UNCLASSIFIED DRUG; 17 HYDROXYPREGNENOLONE; 3 BETA,15 BETA,17 ALPHA TRIHYDROXY 5 PREGNEN 20 ONE; 3 BETA,15 BETA,17 ALPHA-TRIHYDROXY-5-PREGNEN-20-ONE; BORON DERIVATIVE; DRUG DERIVATIVE; GLYCOL; N BUTYLBORONIC ACID; N-BUTYLBORONIC ACID;

ACETYLATION; ADRENAL HYPERPLASIA; ARTICLE; EPOXIDATION; GAS CHROMATOGRAPHY; HUMAN; NUCLEAR MAGNETIC RESONANCE; PERINATAL DEVELOPMENT; STEROID ANALYSIS; STEROID METABOLISM; URINARY EXCRETION; CHEMISTRY; MASS SPECTROMETRY; METABOLISM; METHODOLOGY; NEWBORN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

17-ALPHA-HYDROXYPREGNENOLONE; BORON COMPOUNDS; GLYCOLS; HUMANS; INFANT, NEWBORN; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY;

EID: 0029658970     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0039-128X(95)00169-Q     Document Type: Article

References (20)

1. Joannou GE (1981). Identification of 15β-hydroxylated C21 steroids in the neo-natal period: The role of 3α,15β,17α-trihydroxy-5β-pregnan-20-one in the perinatal diagnosis of congenital adrenal hyperplasia (CAH) due to a 21-hydroxylase deficiency. J Steroid Biochem 14:901-912.
2. Kraan GPB, Wolters BG, Van der Molen JC, Nagel GT, Drayer NM, Joannou GE (1993). New identified 15β-hydroxylated 21-deoxy-pregnanes in congenital adrenal hyperplasia due to 21-hydroxylase deficiency. J Steroid Biochem Mol Biol 45:421-434.
3. Reeder AY (1990). An investigation of the synthesis of 3β,15β,17α-trihydroxy-5-pregnen-20-one and of 3α,15β,17α-trihydroxy-5β-pregnan-20-one. Steroids of fetal origin. Ph.D. Thesis, University of Sydney.
4. Joannou GE (1985). Perinatal adrenal steroidogenesis. Ph.D. Thesis, University of Sydney.
5. Horning EC (1968). Gas phase analytical methods for the study of steroid hormones and their metabolites. In: Eik-Nes KB, Horning EC (eds), Gas Chromatography of Steroids. Springer-Verlag, Berlin, p. 32.
6. Ravi BN, Wells RJ (1982). A series of new diterpenes from the brown alga dilophus-marginatus (Dictyotaceae). Aust J Chem 35: 129-144.
7. Mathre DJ, Jones TK, Xavier LC, Blacklock TJ, Reamer RA, Mohan JJ, Jones ETT, Hoogsteen K, Baum MW, Grabowski EJJ (1991). A practical enantioselective synthesis of α,α-diaryl-2-pyrrolidinemethanol. Preparation and chemistry of the corresponding oxaborolidines. J Org Chem 56:751-762.
8. Matteson DS, Michnick TJ (1990). Stereoselective reaction of an enolate with chiral α-haloboronic acid esters. Organometallics 9: 3171-3177.
9. Brooks CJW, Barrett GM, Cole WJ (1984). Studies of the selective derivatisation of methyl hyocholate and related steroidal ring B diols by gas chromatography-mass spectrometry. J Chromatogr 289:231-248.
10. Mukaiyama T, Yamaguchi M (1982). A stereoselective syntheis of α,β-dihydroxy ketones an aldol reaction of enediol-type cyclic vinyloxyboranes. Chem Lett 509-512.
11. Dahlhoff WV, Geisheimer A, Köster R (1980). Organoboron monosaccharides; IX. Efficient synthesis of a protected α-D-monofuranosyl bromide. Synthesis 935-936.
12. Dahlhoff WV, Köster R (1980). Organoboron-monosaccharides; X. High yield synthesis of a bifunctionally protected α-D-lyxofuranosyl bromide. Synthesis 936-937.
13. Poole CF, Zlatkis A (1980). Cyclic derivatives for the selective chromatographic analysis of bifunctional compounds. J Chromatogr 184:99-183.
14. Poole CF, Singhawangcha S, Zlatkis A (1978). Substituted benzeneboronic acids for the gas chromatographic determination of bifunctional compounds with electron capture detection. J Chromatogr 158:33-41.
15. Gaskell SJ, Brooks CJW (1978). Studies of aldosterone 20,21-cyclic boronates by gas-liquid chromatography and mass spectrometry. J Chromatogr 158:331-336.
16. Brooks CJW, Harvey DJ (1971). Comparative gas chromatographic studies of corticosteroid boronates. J Chromatogr 54:193-204.
17. Synthetic applications of organoboranes. In: Carruthers W (1971), Some Modern Methods of Organic Synthesis, Cambridge University Press, p. 207.
18. Fieser LF, Rajagopalan S (1949). Selective oxidation with N-bromosuccinimide II. Cholestane-3β,5α,6β-triol. J Am Chem Soc 71: 3938-3941.
19. Gravestock MB, Morton DR, Boots SG, Johnson WS (1980). Biomimetric polyene cyclizations. Participation of the methylacetylenic terminator and nitroalkanes. A synthesis of testosterone. J Am Chem Soc 102:800-807.
20. Lewbart M, Schneider JJ (1969). Preparation and properties of steroidal 17,20-and 20,21-acetonides epimeric at C-20. I. Derivatives of 5β-pregnan-3α-ol. J Org Chem 34:3505-3512.