The Structure and Synthesis of D-Homosteroids<sup>1</sup>

Wendler, N. L.; Taub, D.; Dobriner, Shirley; Fukushima, David K.

doi:10.1021/ja01600a061

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Cited by 27 publications

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“…Patchoulene Oxides (24,25).-Patchoulene (10 g., 49 mmoles), obtained by the dehydration of patchouli alcohol with phosphorus oxychloride in pyridine, and chloroform (50 ml.) was placed in a three-neck flask equipped with a thermometer, drying tube and a dropping funnel.…”

Section: Methodsmentioning

confidence: 99%

Terpenes. XVI.^1,2 Constitution of Patchouli Alcohol and Absolute Configuration of Cedrene

Büchi¹,

Erickson²,

Wakabayashi³

1961

J. Am. Chem. Soc.

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Section: Methodsmentioning

confidence: 99%

Terpenes. XVI.^1,2 Constitution of Patchouli Alcohol and Absolute Configuration of Cedrene

Büchi¹,

Erickson²,

Wakabayashi³

1961

J. Am. Chem. Soc.

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The α‐Hydroxy Ketone (α‐Ketol) and Related Rearrangements†

Hofferberth

Paquette

2003

Organic Reactions

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Treatment of suitable alpha‐hydroxy aldehydes and ketones with a base, a Bronsted or Lewis acid, or simply with heat has long been know to induce the 1,2‐shift of an alkyl or aryl substituent to form an isomeric product. The synthetic utility of the process was considerably expanded when applied to steroidal D‐ring homoannulations, and has more recently encompassed novel ring expansion to numerous complex target ring systems. The classical alpha‐ketol rearrangement shares, in common with other base‐promoted ketogenic isomerizations, the property of advancing from an alkoxide to a carbonyl group as the migrating center relocates its bonding electrons to the adjacent trigonal center. A distinctive feature of the title reaction, however, is its reversibility, such that the more stable alpha‐hydroxy carbonyl isomer is favored. The process has sometimes been termed the acyloin rearrangement. This chapter focuses on the isomerization of alpha‐hydroxy ketones, aldehydes, and imines under various reaction conditions exclusive of photochemical activation. The literature coverage extends to 2000. Since many of the steroidal transformations were carried out in early days when products were not always adequately characterized; errors in structural assignment were occasionally made. Experimental detail was sometimes lacking. To alleviate this problem, we have included only experiments that lead to reasonably pure products of established structure.

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Ethylene Oxides

Rosowsky¹

1964

Chemistry of Heterocyclic Compounds: A Series of Monographs

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The Structure and Synthesis of D-Homosteroids¹

Cited by 27 publications

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Terpenes. XVI.^1,2 Constitution of Patchouli Alcohol and Absolute Configuration of Cedrene

Terpenes. XVI.^1,2 Constitution of Patchouli Alcohol and Absolute Configuration of Cedrene

The α‐Hydroxy Ketone (α‐Ketol) and Related Rearrangements†

Ethylene Oxides

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The Structure and Synthesis of D-Homosteroids1

Cited by 27 publications

References 0 publications

Terpenes. XVI.1,2 Constitution of Patchouli Alcohol and Absolute Configuration of Cedrene

Terpenes. XVI.1,2 Constitution of Patchouli Alcohol and Absolute Configuration of Cedrene

The α‐Hydroxy Ketone (α‐Ketol) and Related Rearrangements†

Ethylene Oxides

Contact Info

Product

Resources

About

The Structure and Synthesis of D-Homosteroids¹

Terpenes. XVI.^1,2 Constitution of Patchouli Alcohol and Absolute Configuration of Cedrene

Terpenes. XVI.^1,2 Constitution of Patchouli Alcohol and Absolute Configuration of Cedrene