Total Synthesis of dl-18-Norestrone<sup>1</sup>

Meyer, Walter L.; Cameron, D. D.; Johnson, William S.

doi:10.1021/jo01051a004

Cited by 21 publications

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“…Accordingly, the diene 16a was treated with a limited amount of ozone in methylene chloride (19) at -70". Chromatography of the neutral portion of the product over silica gel gave the ketone 19 in about 10% yield.…”

Section: Traduit Par Le Journal]mentioning

confidence: 99%

“…(CHCI,) 3200-2400 (carboxyl OH), 1730 sh (monomeric carboxyl), 1690 cm-' (dimeric carboxyl); n.m.r. r 9.14 and 9.11 (two three-proton doublets, non-equivalent methyls of isopropyl), 8.88 Meth~~l13-0xo-7,17-secoacon-8(15)-en-13-on-18-oate (19) A solution of diene 16a (48 mg) in methylene chloride was cooled to -70' and a saturated solution of ozone in methylene chloride (6 ml (19)) at -70" was added. The blue color of the ozone solution soon disappeared.…”

Section: Rerluction Of Ketoacid I2amentioning

confidence: 99%

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Rearrangements in the Diterpenoid Series. I. The Solvolysis of Methyl 15β-tosyloxy-13-isopropyl-17-noratis-13-en-18-oate

Ayer¹,

Deshpande²

1973

Can. J. Chem.

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Section: Traduit Par Le Journal]mentioning

confidence: 99%

Section: Rerluction Of Ketoacid I2amentioning

confidence: 99%

Rearrangements in the Diterpenoid Series. I. The Solvolysis of Methyl 15β-tosyloxy-13-isopropyl-17-noratis-13-en-18-oate

Ayer¹,

Deshpande²

1973

Can. J. Chem.

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“…However, if dehydration to 5 was first performed, cyclization gave appreciable quantities of the natural trans-anti-trans 6. Initially this latter sequence gave a 2:1 mixture of 7:6 [3,5], but later experiments [6] showed that 6 (and its demethylated analog) could be made the only readily isolable product (ca. 10%).…”

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A + Cd → Acd → Abcd

1974

Organic Chemistry: A Series of Monographs

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This chapter is divided into six portions according to the type of reaction used in the condensation of the A fragment with the CD portion. The first section concerns the reaction between an anionic A ring with a keto function in the CD portion and discusses, for the most part, Johnson's first estrone synthesis. In Section 7.2 the process is reversed such that an anion formed from the CD portion reacts with A; Section 7.3 discusses the use of the Wittig reaction in steroid total synthesis and includes some recent, promising work by a Russian group as well as brief mention of Inhoffen's classic work in the vitamin D field (a detailed presentation of the latter, as well as some recent work by Lythgoe on the synthesis of calciferol, has been omitted because the products are, for the present purposes, not considered true steroids). Section 7.4 discusses the recent, intriguing use of CD enamines in steroid total synthesis, and Section 7.5 presents the preparation of some thiasteroids. The last section describes some brief, miscellaneous schemes which have been reported in, as yet, little detail. Condensation of Ring-A Anionic Fragments with CD KetonesThe first steroid total synthesis of Johnson resulted in die preparation of seven of the eight possible racemic stereoisomers of estrone and was 142 14 15 16Scheme 7-1 * Lythgoe and his co-workers have recently employed a similar reaction in their extensive researches in the total synthesis of calciferol and its relatives. They utilized lithium acetylides rather than the current potassium salts [4].

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TheDieckmann Condensation (Including theThorpe‐Ziegler Condensation)

Schaefer

Bloomfield

2011

Organic Reactions

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The Dieckman condensation is an acetoacetic ester condensation in which a dicarboxylic ester is cyclized to a beta‐ketonic ester through the action of a base. The dicarboxylic ester must have at least one alpha‐hydrogen atom and the carbalkoxy groups must be situated that cyclization will result in a 4‐membered ring or larger ring. Discovery and development of the reaction are generally credited to Dieckmann, who found that heating an adipic or a pimelic ester with sodium and a trace alcohol led to cyclization with formation of a cyclopentanone or a cyclohexanone. The Dieckmann condensation has proved useful for the preparation of a variety of carbocyclic and heterocyclic ketones and has been extended to the synthesis of 7 and 8‐membered rings.

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Total Synthesis of dl-18-Norestrone¹

Cited by 21 publications

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Rearrangements in the Diterpenoid Series. I. The Solvolysis of Methyl 15β-tosyloxy-13-isopropyl-17-noratis-13-en-18-oate

Rearrangements in the Diterpenoid Series. I. The Solvolysis of Methyl 15β-tosyloxy-13-isopropyl-17-noratis-13-en-18-oate

A + Cd → Acd → Abcd

TheDieckmann Condensation (Including theThorpe‐Ziegler Condensation)

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Total Synthesis of dl-18-Norestrone1

Cited by 21 publications

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Rearrangements in the Diterpenoid Series. I. The Solvolysis of Methyl 15β-tosyloxy-13-isopropyl-17-noratis-13-en-18-oate

Rearrangements in the Diterpenoid Series. I. The Solvolysis of Methyl 15β-tosyloxy-13-isopropyl-17-noratis-13-en-18-oate

A + Cd → Acd → Abcd

TheDieckmann Condensation (Including theThorpe‐Ziegler Condensation)

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Total Synthesis of dl-18-Norestrone¹