Total synthesis of modified steroids—1

France, Donald J.; Hand, John J.; Los, M. G.

doi:10.1016/s0040-4020(01)82935-5

Cited by 14 publications

(7 citation statements)

References 9 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…6 Meanwhile, Kuo et al reinvestigated the bark extracts from T. cryptomerioides, and the structures of taiwaniaquinone F (12) and taiwaniaquinols C (13) and D (14) were reported in 2003. 7a Further study of the bark extract resulted in the 2005 report of taiwaniaquinones G (15) and H (16) and taiwaniaquinols E (17) and F (18). 7b No related abeo-abietane diterpenes have been reported since 2005.…”

Section: Isolationmentioning

confidence: 99%

See 1 more Smart Citation

The Taiwaniaquinoids: A Review

2010

View full text Add to dashboard Cite

A comprehensive overview of the taiwaniaquinoid family of natural products is presented. A summary of the isolation, biosynthesis, and biological activity of these compounds is followed by a discussion of various synthetic strategies to the skeletal framework and a detailed discussion of 12 published syntheses of members of this family. This review covers the literature from the discovery of the first taiwaniaquinoid in 1995 until June 2009.

show abstract

Section: Isolationmentioning

confidence: 99%

“…‡ Dedicated to Professor Paul A. Grieco on the occasion of his 65th birthday. abietanes (1-4, 6, 7, 12-14) or, if a carbon is lost during or after rearrangement, the 6-nor-5(6f7)abeo-abietanes (5,(15)(16)(17)(18). No work has been done to verify this conjecture.…”

Section: Biosynthesis and Classificationmentioning

confidence: 99%

The Taiwaniaquinoids: A Review

2010

View full text Add to dashboard Cite

show abstract

“…The hydrogénation of 133 with its two ß-methyl groups to the 9/3-derivative 134 is inexplicable, however [106].…”

Section: Hydrogénation and Reduction Of Double Bondsmentioning

confidence: 99%

Designing Total Syntheses

1974

Organic Chemistry: A Series of Monographs

View full text Add to dashboard Cite

“…The starting material 43 was readily prepared in 48% yield starting from 2-methylcyclohexane-l,3-dione and ethyl vinyl ketone [25]. The very stable anion of 43 was generated with sodium hydride in dimethoxyethane and alkylated in good yield to provide 44 (84%) or 49 (85%) [26,27]. Use of the phenacyl derivative rather than a phenethyl compound (which was tried but gave no product) circumvented one of the major problems previously encountered in this type of synthesis, i.e., the elimination of HX to form a styrene derivative (vide supra).…”

Section: Joumentioning

confidence: 99%

A + Cd → Acd → Abcd

1974

Organic Chemistry: A Series of Monographs

View full text Add to dashboard Cite

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].

show abstract

Total synthesis of modified steroids—1

Cited by 14 publications

References 9 publications

The Taiwaniaquinoids: A Review

The Taiwaniaquinoids: A Review

Designing Total Syntheses

A + Cd → Acd → Abcd

Contact Info

Product

Resources

About