Total synthesis of zincophorin

Danishefsky, Samuel J.; Selnick, Harold G.; Zelle, Robert E.; DeNinno, Michael P.

doi:10.1021/ja00221a043

Cited by 137 publications

(79 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…[5] In the presence of Lewis acids as catalysts, it has been proposed that the Lewis acid is oriented trans to the carbonyl substituent and that the modest endo-selectivity observed in most cases is due to a preference for the solvated Lewis acid being exo because of its size. [6] However, when discussing the stereochemical course of HDA reactions, it is important to note that the configuration of the diene in the ground state does not necessarily have to be the same as that of the reacting diene. [7] Compared to the numerous theoretical calculations on the normal DA reaction, only very few theoretical studies of HDA reactions have been performed, [8] and even fewer on Lewis acid catalyzed HDA reactions.…”

Section: Reviewsmentioning

confidence: 99%

“…[18,19] Performing the reaction of benzaldehyde 2 a with Danishefskys diene 3 a leads to the formation of the HDA adduct 4 a in the presence (R)-12 c ± f in up to 97 % yield and 99.4 % ee using (R)-12 e as the catalyst [Eq. (6)]. A clear trend appears: ligand (R)-12 c, which has neither the steric bulk, nor the coordinating ether oxygen atoms characteristic of (R)-12 e, catalyzes the reaction, but only modest chemical and optical yields of 4 a are obtained.…”

Section: Chiral Aluminum and Boron Complexesmentioning

confidence: 99%

See 1 more Smart Citation

Catalytic Asymmetric Hetero-Diels–Alder Reactions of Carbonyl Compounds and Imines

Jørgensen

2000

Angew. Chem. Int. Ed.

631

145

View full text Add to dashboard Cite

Asymmetric catalysis is a challenge for chemists: How can we design catalysts to achieve the goal of forming optically active compounds? This review provides the reader with an overview of the development of catalytic asymmetric hetero‐Diels–Alder reactions of carbonyl compounds and imines. Since its discovery, the Diels–Alder reaction has undergone intensive development and is of fundamental importance for synthetic, physical, and theoretical chemists. The Diels–Alder reaction has been through different stages of development, and at the beginning of the 21st century catalytic Diels–Alder reactions are one of the main areas of focus. The preparation of numerous compounds of importance for our society is based on cycloaddition reactions to carbonyl compounds and imines. There are several parallels between the reactions of carbonyl compounds and those of imines, which, however, begin to vanish on entering the field of catalytic reactions. Why? From a mechanistic point of view some similarities can be drawn, but the synthetic development of catalytic enantioselective hetero‐Diels–Alder reactions of imines are several years behind those of the carbonyl compounds. For hetero‐Diels–Alder reactions of carbonyl compounds there a number of different chiral catalysts, and great progress has been achieved in developing enantioselective reactions for unactivated and activated carbonyl compounds. In contrast the development of catalytic enantioselective hetero‐Diels–Alder reactions of imines is in its infancy and only few catalytic reactions have been published. This review will focus on the most important developments, and discuss the synthetic and mechanistic aspects of enantioselective hetero‐Diels–Alder reactions of carbonyl compounds catalyzed by chiral Lewis acids. For the hetero‐Diels–Alder reactions of imines, the diastereoselective reactions of optically substrates catalyzed by Lewis acids will be presented first, followed by the catalytic enantioselective reactions.

show abstract

Section: Reviewsmentioning

confidence: 99%

Section: Chiral Aluminum and Boron Complexesmentioning

confidence: 99%

Catalytic Asymmetric Hetero-Diels–Alder Reactions of Carbonyl Compounds and Imines

Jørgensen

2000

Angew. Chem. Int. Ed.

631

145

View full text Add to dashboard Cite

show abstract

“…[1] As a rule, functionalized dihydropyrans are synthesized by multi-step protocols via anionic, [2] cationic [3] or radical [4] cyclization, hetero-Diels-Alder cycloaddition, [5] dioxanone Claisen rearrangement, [6] and ring-closing metathesis of enol ethers. [7] Unlike the above approaches, in this work, we have assembled the functionalized 3,4-dihydropyrans essentially in a one-pot procedure from cheap and available starting materials (ketones and acetylene) in excellent yields.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Functionalized 3,4‐Dihydropyrans via Rearrangement of the Products of a One‐Pot Diastereoselective Assembly of Ketones and Acetylene

Schmidt¹,

Трофимов²,

Zorina³

et al. 2010

Eur J Org Chem

View full text Add to dashboard Cite

show abstract

“…In particular, 1,2-unsaturated derivatives Ϫ the so-called glycals Ϫ are starting materials in a variety of transformations. [17,18] More recently, metal-mediated approaches to these cyclic enolethers have been developed. The cyclization of acetylenic alcohols at a metal template yields 2,3-dihydrofurans or 2,3-dihydropyrans, either directly [19] or via a carbene complex intermediate, which is subsequently cleaved by action of a base.…”

Section: Introductionmentioning

confidence: 99%

A Synthesis of Densely Functionalized 2,3-Dihydropyrans Using Ring-Closing Metathesis and Base-Induced Rearrangements of Dihydropyran Oxides

Schmidt

Wildemann

2000

Eur. J. Org. Chem.

View full text Add to dashboard Cite

The preparation of dihydropyran and dihydrofuran oxides and their rearrangement in the presence of lithium dialkylamides to functionalized 2,3‐dihydropyrans or 2,3‐dihydrofurans, respectively, is described. The regiochemical outcome of the reaction can be influenced by the relative configuration of the starting epoxides and the steric demand of the base. The 2,3‐dihydropyrans obtained were converted stereoselectively to difunctionalized 3,4‐dihydropyrans by the carbon‐Ferrier reaction, or to fused acetals by addition of dimedone, mediated by ceric ammonium nitrate. The stereochemical results are rationalized by mechanistic proposals.

show abstract

Total synthesis of zincophorin

Cited by 137 publications

References 0 publications

Catalytic Asymmetric Hetero-Diels–Alder Reactions of Carbonyl Compounds and Imines

Catalytic Asymmetric Hetero-Diels–Alder Reactions of Carbonyl Compounds and Imines

Synthesis of Functionalized 3,4‐Dihydropyrans via Rearrangement of the Products of a One‐Pot Diastereoselective Assembly of Ketones and Acetylene

A Synthesis of Densely Functionalized 2,3-Dihydropyrans Using Ring-Closing Metathesis and Base-Induced Rearrangements of Dihydropyran Oxides

Contact Info

Product

Resources

About