The Total Synthesis of Diacetyloxodenudatine

Wiesner, K.; SETHI, S. P.; Sterzycki, Roman Z.; Sy, Wing Wah; Martini-Bettolo, Rinaldo; Tsai, T. Y. R.

doi:10.3987/r-1980-01-0023

Cited by 14 publications

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ThePeterson Olefination Reaction

Ager¹

1990

Organic Reactions

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The Peterson olefination reaction provides a useful method for the preparation of alkenes from α‐silyl carbanions and carbonyl compounds. As alkenes hold a pivotal role in synthetic methodology for the introduction of vicinal functionality, particularly in a stereoselective manner, the Peterson reaction is increasing in importance in the reaction repertoire. This chapter discusses the reaction and its advantages over comparable methods such as the Wittig reaction. Although elimination of β‐silylalkoxides, was noted in 1947, it was not until Peterson described the preparation of functionalized alkenes from α‐silyl carbanions in 1968 that the full potential of the reaction became apparent. Alkenes are usually only isolated directly from the condensation when an anion‐stabilizing group is present in the carbanion; if not, the β‐hydroxysilane is formed. Many examples of the formation of alkenes from β‐hydroxysilanes are cited in the literature. These eliminations are discussed in this chapter, although they strictly should not be called Peterson olefination reactions. However, the “common” organic reactions of β‐hydroxysilanes which follow the usual pathways—such as the thermolytic elimination of esters derived from those alcohols—are omitted. The central nature of the Peterson reaction to organosilicon chemistry has led all reviews in this area to discuss the subject to some extent. In addition, the reaction itself has been reviewed previously.

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ThePeterson Olefination Reaction

Ager¹

1990

Organic Reactions

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TheBaeyer–VilligerOxidation of Ketones and Aldehydes

1993

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The oxidative conversion of alicyclic ketones into lactones with permonosulfuric acid was discovered by Baeyer and Villiger in 1899, and in their honor the general process by which ketones are converted into esters or lactones is now known as the Baeyer–Villiger reaction. The literature on this synthetically useful process has been reviewed comprehensively through 1953 in Volume 9 of Organic Reactions , and less comprehensive reviews of the reaction have appeared since then. More recent investigations have led to the development of new synthetic reagents, to improvements in experimental reaction conditions, and to a better understanding of regiochemical and stereochemical aspects of the reaction. Baeyer–Villiger reactions now often can be carried out with functional group chemoselectivity and regiochemical control. Although the recent removal from commerce of 90% hydrogen peroxide and reagents based upon this oxidant are a setback to Baeyer–Villiger reaction methodology, alternative reagents, catalysts, and methods described in this review are available to fill the gaps. The definition of the Baeyer–Villiger reaction is somewhat fuzzy, and can be considered to include both ketones and aldehydes. In addition to the traditional use of organic and inorganic peracids as oxidants, examples of oxygen insertion reactions using hydrogen peroxide, alkyl peroxides, and several metal ion oxidants are considered to fall within the scope of this chapter and are included in the tabular survey.

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Ongoing Pursuit of Diterpenoid Alkaloids: A Synthetic View

Liu

Qin

2015

Asian J Org Chem

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The incorporation of nitrogen atoms into policyclic diterpenes has led to one of the most fascinatingg roup of natural products with cage-like structures:d iterpenoid alkaloids. Their singular architectural features and significant bioactivitiesm ade them highly pursued targets amongst the synthetic community over decades. At otal of seven types of diterpenoid alkaloid molecules have been synthesized thus far,a nd the research in this area experiencedanew climax in the past five years. With ab rief overview and summary of the historic achievements, this Focus Review particularly covers the recent,post-2010 advances in the field of diterpenoid alkaloid synthesis, highlighting the utilizationofinnovative synthetic methods and strategies. Despite numerous achievements, there are stillanumber of such alkaloids with differenta nd uniques tructural types waiting to be accomplished, implying that the pursuit is far from ending.

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The Total Synthesis of Diacetyloxodenudatine

Cited by 14 publications

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ThePeterson Olefination Reaction

ThePeterson Olefination Reaction

TheBaeyer–VilligerOxidation of Ketones and Aldehydes

Ongoing Pursuit of Diterpenoid Alkaloids: A Synthetic View

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