Steroid Total Synthesis—Hydrochrysene Approach. V.<sup>1</sup> Introduction of Oxygen at the 11-Position

Johnson, William S.; Kemp, A. D.; Pappo, Raphael; Ackerman, James H.; Johns, William F.

doi:10.1021/ja01605a018

Cited by 24 publications

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“…In previous papers we have described the stereoselective preparation of the cis-anti-trans-alcohol IV from the tetracyclic ketone II by the following steps: hydrogenation of the 4,5-(steroid numbering) double bond over palladium,3 reduction of the keto group with lithium aluminum hydride,3 and finally reduction of the 8,9-(styrene) double bond with potassium and alcohol in ammonia. 4 In the present work reduction of this product (IV) with lithium-ammonia-alcohol under vigorous condi-tions6 afforded, after acid hydrolysis of the enol ethers, a mixture of the 13,14-dehydro ketone V, m.p. 137-138°, Xmax 248 µ and the 16,17-dehydro ketone VI, m.p.…”

mentioning

confidence: 64%

Steroid Total Synthesis—Hydrochrysene Approach. Part XII.¹ An Alternative Route to Testosterone. The Synthesis of l-Testosterone and of dl-13-Isotestosterone

Johnson¹,

Vredenburgh²,

Pike³

1960

J. Am. Chem. Soc.

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confidence: 64%

Steroid Total Synthesis—Hydrochrysene Approach. Part XII.¹ An Alternative Route to Testosterone. The Synthesis of l-Testosterone and of dl-13-Isotestosterone

Johnson¹,

Vredenburgh²,

Pike³

1960

J. Am. Chem. Soc.

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“…Our initial investigations on the transformation of olefin 12 to the secodialdehyde (15) In all instances the yield of 16 was very low. On the other hand, hydroxylation with osmium I tetroxide proceeded smoothly to provide both 1 possible 11,12-diols (14 and 15).…”

Section: Figmentioning

confidence: 95%

Synthetic Studies in the Veratrum Alkaloid Series. I. Introduction and the Total Synthesis of Appropriate C-Nor-D-homo Steroid Derivatives

Kutney¹,

By²,

Cable³

et al. 1975

Can. J. Chem.

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“…With a procedure at hand for elaboration of the natural (racemic) steroid skeleton, a significant effort was directed toward establishing methods for introducing oxygen substituents at C-ll [51,58,59]. As outlined in Schemes 12-8 and 12-9, the goal was reached, but the reactions often yielded several components and/or provided the intended product in lowered amounts.…”

Section: Meneta I" Omementioning

confidence: 99%

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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Steroid Total Synthesis—Hydrochrysene Approach. V.¹ Introduction of Oxygen at the 11-Position

Cited by 24 publications

References 0 publications

Steroid Total Synthesis—Hydrochrysene Approach. Part XII.¹ An Alternative Route to Testosterone. The Synthesis of l-Testosterone and of dl-13-Isotestosterone

Steroid Total Synthesis—Hydrochrysene Approach. Part XII.¹ An Alternative Route to Testosterone. The Synthesis of l-Testosterone and of dl-13-Isotestosterone

Synthetic Studies in the Veratrum Alkaloid Series. I. Introduction and the Total Synthesis of Appropriate C-Nor-D-homo Steroid Derivatives

Cd → BCD → Abcd

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Steroid Total Synthesis—Hydrochrysene Approach. V.1 Introduction of Oxygen at the 11-Position

Cited by 24 publications

References 0 publications

Steroid Total Synthesis—Hydrochrysene Approach. Part XII.1 An Alternative Route to Testosterone. The Synthesis of l-Testosterone and of dl-13-Isotestosterone

Steroid Total Synthesis—Hydrochrysene Approach. Part XII.1 An Alternative Route to Testosterone. The Synthesis of l-Testosterone and of dl-13-Isotestosterone

Synthetic Studies in the Veratrum Alkaloid Series. I. Introduction and the Total Synthesis of Appropriate C-Nor-D-homo Steroid Derivatives

Cd → BCD → Abcd

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Steroid Total Synthesis—Hydrochrysene Approach. V.¹ Introduction of Oxygen at the 11-Position

Steroid Total Synthesis—Hydrochrysene Approach. Part XII.¹ An Alternative Route to Testosterone. The Synthesis of l-Testosterone and of dl-13-Isotestosterone

Steroid Total Synthesis—Hydrochrysene Approach. Part XII.¹ An Alternative Route to Testosterone. The Synthesis of l-Testosterone and of dl-13-Isotestosterone