Total Synthesis of Phoslactomycin A

König, Christian M.; Gebhardt, Björn; Schleth, Cornelia; Dauber, Mario; Koert, Ulrich

doi:10.1021/ol900757k

Cited by 47 publications

(15 citation statements)

References 29 publications

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“…To date, five formal/total synthesis of PLMs have been reported. Similarly, leuctroducsin B has been a target of interest for the synthetic community .…”

Section: Introductionmentioning

confidence: 99%

“…Similarly, leuctroducsin B has been a target of interest for the synthetic community . Evans aldol reaction,, Brown‐type pentenylation, and [2,3]‐Wittig rearrangement have been used to control the configuration at the C‐4 and C‐5 stereocentres. The 1,2‐diol at C‐8–C‐9 has been installed by Sharpless asymmetric dihydroxylation, or chelation‐controlled addition to a ketone,, and in all the syntheses, the C‐13–C‐14 bond was constructed using a Stille coupling.…”

Section: Introductionmentioning

confidence: 99%

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A Stereoselective Synthesis of the Carbon Backbone of Phoslactomycin B

Raghavan

Patel

2017

Eur J Org Chem

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A convergent synthesis of the entire carbon framework of phoslactomycin B is disclosed. An initial route aimed to create the C‐8 tetrasubstituted stereocentre through regioselective intermolecular coupling between an internal alkyne and an allyl silyl ether, adopting Trost's protocol, followed by [2,3] sigmatropic rearrangement. But this was not successful. In a second approach, a propargylic sulfide was rearranged to give an unsaturated ketone. This was then treated with lithio acetonitrile to create the C‐8 stereocentre selectively. The C‐4 and C‐5 stereocentres were introduced by a non‐Evans syn‐aldol reaction using Crimmins's protocol. The C‐9 and C‐11 carbinol centres were created by asymmetric transfer hydrogenation. The (Z,Z)‐diene moiety was introduced by partial reduction of a diyne following Hansen's modification of the Boland reduction reaction.

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“…To date, five formal/total synthesis of PLMs have been reported. Similarly, leuctroducsin B has been a target of interest for the synthetic community .…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

A Stereoselective Synthesis of the Carbon Backbone of Phoslactomycin B

Raghavan

Patel

2017

Eur J Org Chem

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“…216 Under certain circumstances, cinnamate 215 can be generated as a by-product. Thus the mechanism for the formation of 211 via double arylation most probably follows a cascade sequence involving 1,4-addition/b-oxygen elimination [217][218][219][220][221][222][223][224] to afford 215 with subsequent 1,4-addition/protonation (Scheme 107). The lack of a common 1,4-addition product in the reaction mixture (detected by TLC) confirms that elimination of the b-oxygen smoothly occurs, which in turn indicates the possible protonation of intermediate 213 was completely over ruled.…”

Section: Table 48mentioning

confidence: 99%

Rh-catalyzed asymmetric 1,4-addition reactions to α,β-unsaturated carbonyl and related compounds: an update

Heravi

Dehghani

Zadsirjan

2016

Tetrahedron: Asymmetry

106

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Rh-catalyzed asymmetric 1,4-addition reactions to a,b-unsaturated carbonyl and related compounds: an update Available online xxxx Dedicated to my son, OMID on the occasion of his 35th birthday. a b s t r a c tThe Rh-catalyzed asymmetric 1,4-addition of organometallic reagents to an appropriate receptor has been a growing area of research over the last decade. The receptors for such a 1,4-addition reaction are chiefly a,b-unsaturated ketones, esters, amides, enones, nitroalkenes, and occasionally phosphonates etc. This reaction in the presence of chiral rhodium complexes introduce the aryl and alkenyl groups at the b-position of the above electron poor olefins, enantioselectively. Chiral Rh complexes similar to other transition metals can be added to some electron poor olefins, in turn making them viable to attack by various organometallic reagents for highly enantioselective C-C bond formation. The Rh-catalyzed asymmetric 1,4-addition of organometallic reagents to electron poor olefins has been reviewed in 2003. Due to the importance of the asymmetric C-C bond formation via 1,4-conjugate addition reactions and the number of such reactions catalyzed by Rh-complexes, in this review we highlight the recent advances in Rh-complex asymmetric catalyzed 1,4-addition reactions since 2003.

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“…In addition, such antagonistic and agonistic compounds also provide useful lead compounds for drug discovery. In this context, we focused on the synthesis of dysiherbaine (37), neodysiherbaine A (38), and kaitocephalin (39). The total syntheses of dysiherbaine (37) and kaitocephalin (39) are presented here.…”

Section: Synthesis Of Glutamate Receptor Agonists and Antagonistsmentioning

confidence: 99%

Total Synthesis of Biologically Active Natural Products Based on Highly Selective Synthetic Methodologies

Hatakeyama

2014

CHEMICAL & PHARMACEUTICAL BULLETIN

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Total syntheses of structurally and biologically intriguing natural products relying on new synthetic methodologies are described. This article features cinchona alkaloid-catalyzed asymmetric Morita-BaylisHillman reactions, heterocycle syntheses based on rhodium-catalyzed C-H amination and indium-catalyzed Conia-ene reactions, and their utilization for the syntheses of the phoslactomycin family of antibiotics, glutamate receptor agonists and antagonists, and alkaloids with characteristic highly substituted pyrrolidinone core structures.

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Total Synthesis of Phoslactomycin A

Cited by 47 publications

References 29 publications

A Stereoselective Synthesis of the Carbon Backbone of Phoslactomycin B

A Stereoselective Synthesis of the Carbon Backbone of Phoslactomycin B

Rh-catalyzed asymmetric 1,4-addition reactions to α,β-unsaturated carbonyl and related compounds: an update

Total Synthesis of Biologically Active Natural Products Based on Highly Selective Synthetic Methodologies

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