Totalsynthese des Aldosterons. B. (18 → 11)‐Lacton der <i>d,l</i>‐Δ<sup>5</sup>‐3‐Äthylendioxy‐11β‐hydroxy‐20‐oxo‐pregnen‐18‐säure. Über Steroide, 148. Mitteilung

Schmidlin, Julius; Anner, G.; Billeter, J. R.; Heusler, K.; Ueberwasser, H.; Wieland, P.; Wettstein, A.

doi:10.1002/hlca.19570400530

Cited by 30 publications

(5 citation statements)

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“…Partial equilibration to the 17/?-epimer could be effected under various conditions including methoxide catalysis. At this point, the work converged with that of Wettstein and his collaborators who had obtained both epimers and converted the 17/?-analog of 88 to aldosterone [77][78][79]. Johnson, however, developed an alternative procedure utilizing the 17a:-epimer.…”

Section: Meneta I" Omementioning

confidence: 65%

Cd → BCD → Abcd

1974

Organic Chemistry: A Series of Monographs

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The starting CD intermediates for the various total syntheses outlined in this chapter and in Chapter 7 are often the same or quite analogous. Historically, a large effort has been expended in the preparation of such material, both in the context of steroid synthesis and, recently, as a goal unto itself. A discussion of the pathways developed for the synthesis of CD intermediates has been included at this point such that later, when the individual total synthetic schemes are presented, it will be unnecessary to outline the preparation of the starting materials, except in those cases where unique pathways have been developed.Most of the early synthetic plans started with appropriate naphthalene derivatives which in turn gave rise to D-homosteroids. For example, Johnson's estrone synthesis started with decalin-l,5-dione (3, Scheme 12-1) which had earlier been prepared from 1,5-dihydroxynaphthalene (58%) [1], By modifying the previously employed conditions to include Raney nickel hydrogénation at elevated temperatures and pressures in a basic ethanolic solution, it was possible to obtain a mixture of diols, 2 (stereochemistry undetermined), which, without purification, could be oxidized to a mixture of eis and trans diketones 3 [2], The yield for this conversion (l-»3) was 55% and, for synthetic purposes, the mixture 239 O OH J Φ-,ύ^.

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Section: Meneta I" Omementioning

confidence: 65%

Cd → BCD → Abcd

1974

Organic Chemistry: A Series of Monographs

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“…The starting material in the total synthesis of aldosterone [61,[66][67][68] by Schmidlin, Anner, Billeter, and Wettstein was the Sarett's ketone 50 (Scheme 9-9). Condensation of this compound with ethyl carbonate afforded the keto ester 81, w T hich was alkylated with methallyl iodide to give the substituted keto ester 82.…”

Section: Wettsteins First Synthesis Of Aldosteronementioning

confidence: 99%

“…Oxidation of this product 84 with osmium tetroxide led to a mixture of triols 86, which upon selective hydrogénation, afforded the vinylcarbinols 87. The latter were converted into a mixture of cis-transisomeric aldehyde 88, by successive treatment with periodic acid and phosphorous tribromide [61,67]. In an alternative method [67], the compound 84 was ozonized to give the hydroxy ketone 85.…”

Section: Wettsteins First Synthesis Of Aldosteronementioning

confidence: 99%

“…The latter were converted into a mixture of cis-transisomeric aldehyde 88, by successive treatment with periodic acid and phosphorous tribromide [61,67]. In an alternative method [67], the compound 84 was ozonized to give the hydroxy ketone 85. Selective hydrogénation, followed by hydrolysis led to the keto aldehyde 88.…”

Section: Wettsteins First Synthesis Of Aldosteronementioning

confidence: 99%

“…The intensive search by the Ciba group for a better method of the synthesis of aldosterone [66][67][68][69][70][71][72][79][80][81][82][83][84][85][86][87][88][89][90][91][92][93] finally culminated in the announcement of their second synthesis [64,65] of this hormone in 1957-1958 (Scheme 9-12). Alkylation of the Sarett's ketone 50 with methallyl iodide [91] led to a dialkyl derivative 114.…”

Section: Wettsteins Second Synthesis Of Aldosteronementioning

confidence: 99%

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