- Synthesis of (-)-astrogorgiadiol
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Reaction of Rh2(S)-PTPA4 with the (R)-citronellol-derived α-diazo-β-ketoester 1 led to the formation of cyclic β-ketoester 2 in 95% yield and 48% diastereomeric excess. The purity of 2 was increased to >99% de after one crystallization. To demonstrate its utility in steroid total synthesis, the β-ketoester 2 was carried on to secosteroid (-)-astrogorgiadiol (3), a naturally occuring vitamin D analogue with antiproliferative properties.
- Taber,Malcolm
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p. 944 - 953
(2007/10/03)
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- Synthesis Based on Cyclohexadienes. V. A New Approach to the Synthesis of A-Ring Aromatic Steroids: a Formal Total Synthesis of (+/-)-Estrone
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A new strategy for the construction of A-ring aromatic steroids which resulted in the formal total synthesis of estrone is described.Thus reaction of the adduct (9), obtained from 1-methoxy-4-methylcyclohexa-1,4-diene and acrolein, with 3-(m-methoxyphenyl
- Rao, G. S. R. Subba,Banerjee, D. K.,Devi, L. Uma,Sheriff, Uma
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p. 187 - 203
(2007/10/02)
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- A HIGHLY CONVERGENT AND FLEXIBLE STRATEGY FOR THE SYNTHESIS OF A-RING AROMATIC STEROIDS
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Using Hendrickson's criteria for systematic synthesis design, a strategy featuring a linear six carbon synthon (7) for bis-annulation has been devised for economic, flexible and highly convergent syntheses of A-ring aromatic steroids.
- Mander, Lewis N.,Turner, John V.
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p. 3683 - 3686
(2007/10/02)
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- TOTAL SYNTHESIS OF STEROIDS. PART XV. A NOVEL METHOD OF SYNTHESIS OF β-AMINO KETONES AND VINYL KETONES AND ITS APPLICATION IN TOTAL SYNTHESIS OF ESTROGENS
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A new method of synthesizing β-bromo ketones, vinyl ketones and β-N,N-dimethylamino ketones, starting from terminal olefines, diborane and 1-diazo-4-bromo-2-butanone has been described.The above method was utilized in total synthesis of estrogens.
- Daniewski, Andrzej R.,Jinaraj, V. K.,Kocor, Marian
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p. 2243 - 2246
(2007/10/02)
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- Synthesis of gon-4-enes
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1. A therapeutic composition having progestational activity comprising as active ingredient a 17-aliphatic carboxylic acid ester of 17α-ethynyl-18-methyl-19-nortestosterone and a pharmaceutical carrier for said compound.
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- Synthesis of 13-alkyl-gon-4-ones
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The preparation of 13-methylgon-4-enes and novel 13-polycarbonalkylgon-4-enes by a new total synthesis is described. 13-Alkylgon-4-enes having progestational, anabolic and androgenic activities are prepared by forming a tetracylic gonane structure unsaturated in the 1,3,5(10),9(11) and 14-positions, selectively reducing in the B- and C-rings, and converting the aromatic A-ring compounds so-produced to gon-4-enes by Birch reduction and hydrolysis.
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