Helioporins: bioactive diterpenes from the blue coral Heliopora coerulea

Tanaka, Junichi; Ogawa, Naoya; Liang, Jian; Higa, Tatsuo; Gravalos, D. G.

doi:10.1016/s0040-4020(01)80325-2

Cited by 41 publications

(28 citation statements)

References 13 publications

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“…The use of monosubstituted allenes (products 19 and 20 ) proceeds well in slightly lower yields, which can be attributed to decreased nucleophilicity of the allene nucleophile. Tricyclic cycloadduct 21 was achieved through use of the corresponding tetralone derived allenes and provided rapid access to the core structure of the pseudopterosin family of natural products such as helioporin E. 5b Reaction of allenes with different electronic properties are tolerated (products 23 and 24 ); however, regioisomers are generated in the formation of 24 .…”

Section: Resultsmentioning

confidence: 99%

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An unexpected Lewis acid catalyzed Diels-Alder cycloaddition of aryl allenes and acrylates

Conner

Brown

2016

Tetrahedron

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Section: Resultsmentioning

confidence: 99%

“…The products generated by this method readily map onto the structures of several natural products, 3 and 4 are representative (Scheme 1C). 5 …”

Section: Introductionmentioning

confidence: 99%

An unexpected Lewis acid catalyzed Diels-Alder cycloaddition of aryl allenes and acrylates

Conner

Brown

2016

Tetrahedron

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“…The application of Cu(I)‐catalyzed AAS of cinnamyl chloride with methylmagnesium bromide using a chiral phosphine‐phosphite ligand to set up the first chirality center for the total synthesis of 302 and 303 was accomplished. Two diterpenes possess a serrulatane or amphilectane skeleton, which has proven to act as antiviral and cytotoxic [221] . In 2012, Schmalz et al.…”

Section: Copper‐catalyzed Aas Reactionsmentioning

confidence: 99%

Applications of Transition‐Metal‐Catalyzed Asymmetric Allylic Substitution in Total Synthesis of Natural Products: An Update

Mohammadkhani

Heravi

2020

The Chemical Record

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Metal‐catalyzed asymmetric allylic substitution (AAS) reaction is one of the most synthetically useful reactions catalyzed by metal complexes for the formation of carbon‐carbon and carbon‐heteroatom bonds. It comprises the substitution of allylic substrates with a wide range of nucleophiles or SN2′‐type allylic substitution, which results in the formation of the above‐mentioned bonds with high levels of enantioselective induction. AAS reaction tolerates a broad range of functional groups, thus has been successfully applied in the asymmetric synthesis of a wide range of optically pure compounds. This reaction has been extensively used in the total synthesis of several complex molecules, especially natural products. In this review, we try to highlight the applications of metal (Pd, Ir, Mo, or Cu)‐catalyzed AAS reaction in the total synthesis of the biologically active natural products, as a key step, updating the subject from 2003 till date.

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“…In addition, the stereochemical features associated with some of the advanced intermediates (e. g., alcohol 14a ) are common to a number of important diterpenes including pseudopteroxazole, 5b,20 colombiasin A, 5c,21 elisabethin A, 5e,22a elisapterosin B 5d,22b and helioporins. 23 With the stereochemical issues largely resolved, it should now be possible to design expeditious entry into these molecules and their congeners. Such studies are currently in progress.…”

Section: Stereoselective Installation the C1 Side-chain Of Pseudoptermentioning

confidence: 99%

Ethylene in Organic Synthesis. Repetitive Hydrovinylation of Alkenes for Highly Enantioselective Syntheses of Pseudopterosins

2011

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In this report we highlight the significant potential of ethylene as a reagent for the introduction of a vinyl group with excellent stereoselectivity at three different stages in the synthesis of a broad class of natural products, best exemplified by syntheses of pseudopterosins. The late-stage applications of the asymmetric hydrovinylation reaction further illustrate the compatibility of the catalyst with complex functional groups. We also show that depending on the choice of the catalyst, it is possible to either enhance or even completely reverse the inherent diastereoselectivity in the reactions of advanced chiral intermediates. This should enable the synthesis of diastereomeric analogs of several classes of medicinally relevant compounds that are not readily accessible by the existing methods, which depend on ‘substrate-control’ for the installation of many of the chiral centers, especially in molecules of this class.

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Helioporins: bioactive diterpenes from the blue coral Heliopora coerulea

Cited by 41 publications

References 13 publications

An unexpected Lewis acid catalyzed Diels-Alder cycloaddition of aryl allenes and acrylates

An unexpected Lewis acid catalyzed Diels-Alder cycloaddition of aryl allenes and acrylates

Applications of Transition‐Metal‐Catalyzed Asymmetric Allylic Substitution in Total Synthesis of Natural Products: An Update

Ethylene in Organic Synthesis. Repetitive Hydrovinylation of Alkenes for Highly Enantioselective Syntheses of Pseudopterosins

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