Efficient Synthesis of (−)-<i>trans</i>-Kumausyne via Tandem Intramolecular Alkoxycarbonylation−Lactonization

Boukouvalas, John; Fortier, G; Radu, Ioan-Iosif

doi:10.1021/jo972066r

Cited by 65 publications

(31 citation statements)

References 21 publications

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“…Protection of dimethyl tartrate as acetonide with dimethoxypropane in the presence of p-toluenesulfonic acid followed by treatment with N-methylmethoxyhydroxylamine and an excess of AlMe 3 afforded the bis-Weinreb amide [12] 16 in 72 % overall yield. Amide 16 reacted with an excess of phenylmagnesium bromide in THF to afford the 1,4-diketone 17a in 47 % yield (unoptimized), whereas alkyl deriv-ative 17b was obtained from 16 by treatment with n-heptylmagnesium bromide in THF in 78 % yield.…”

Section: Reformatsky-type Reaction With Functionalized Aldehydesmentioning

confidence: 99%

A New Access to Enantiopure syn‐ and anti‐2‐Methyl‐1,3‐diol Moieties from Chiral Nonracemic α‐Bromo α′‐Sulfinyl Ketones Promoted by Samarium Diiodide

Colobert¹,

Obringer²,

Solladié³

2006

Eur J Org Chem

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Keywords: Asymmetric synthesis / Reformatsky reaction / 2-Methyl-1,3-diol moiety / Sulfoxides / Samarium syn-and anti-2-Methyl-1,3-diols have been prepared by a two-step sequence that involves a SmI 2 -promoted stereoselective Reformatsky addition of chiral nonracemic α-bromo αЈ-sulfinyl ketones to various aldehydes followed by stereoselective reduction of the Reformatsky adduct. The absolute configuration of the products was determined by comparison with literature data and by 1 H NMR NOESY experiments.

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Section: Reformatsky-type Reaction With Functionalized Aldehydesmentioning

confidence: 99%

A New Access to Enantiopure syn‐ and anti‐2‐Methyl‐1,3‐diol Moieties from Chiral Nonracemic α‐Bromo α′‐Sulfinyl Ketones Promoted by Samarium Diiodide

Colobert¹,

Obringer²,

Solladié³

2006

Eur J Org Chem

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“…459 The synthesis features Pd(II)-mediated intramolecular alkoxycarbonylation-lactonization of an enediol to afford the bicyclic lactone core of the key intermediate (403f) in an atom-economical fashion.…”

Section: Synthesis Of C 15 -Acetogenins (Acgs)mentioning

confidence: 99%

Halogenated Organic Molecules of Rhodomelaceae Origin: Chemistry and Biology

et al. 2013

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“…From here the synthesis is reported [18,27] for (À )-trans-kumausyne (1), thus completing its formal synthesis. The Sharpless method allowed epoxidation conditions to be chosen for the correct syn-tetrahydofuran formation via epoxide opening.…”

Section: Methodsmentioning

confidence: 57%

“…Boukouvalas et al [27] in 1998 achieved a remarkable and concise synthesis of (À )-trans-kumausyne (1) via tandem intramolecular alkoxycarbonylation-lactonization strategy for 2,5-cis-THF moiety (Scheme 5). Their approach began with the selective reduction of dimethyl (R)-malate 40 to the diol and primary alcohol silylation as TBDPS ether gave 41 that was further converted into Weinreb's amide 42.…”

Section: Total Synthesis Of (à )-Trans-kumausyne (1)mentioning

confidence: 99%

Advances in Total Synthesis of Some 2,3,5‐Trisubstituted Tetrahydrofuran Natural Products

Fernandes

Pathare

Gorve

2020

Chemistry An Asian Journal

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2,3,5‐Trisubstituted tetrahydrofuran moiety is ubiquitous in natural products. These have served as appealing candidates for total synthesis due to their varied bio‐ and pharmaceutical activities. This tutorial review delineates the ingenious efforts by many researchers in the total synthesis of selected natural products based on a common 2,3,5‐trisubstituted tetrahydrofuran core structure. Many of the syntheses display nuanced interplay between new methods and the ingenuity of planned strategies achieved through catalysis or cascade chemistry. In some cases, the chiron approach has come quite handy, wherein the structural features and the stereochemistry in select molecules could map well with naturally available starting materials. This compilation also aims to enhance the diversity space based on these natural products and further interest in sustainable total synthesis.

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Efficient Synthesis of (−)-trans-Kumausyne via Tandem Intramolecular Alkoxycarbonylation−Lactonization

Cited by 65 publications

References 21 publications

A New Access to Enantiopure syn‐ and anti‐2‐Methyl‐1,3‐diol Moieties from Chiral Nonracemic α‐Bromo α′‐Sulfinyl Ketones Promoted by Samarium Diiodide

A New Access to Enantiopure syn‐ and anti‐2‐Methyl‐1,3‐diol Moieties from Chiral Nonracemic α‐Bromo α′‐Sulfinyl Ketones Promoted by Samarium Diiodide

Halogenated Organic Molecules of Rhodomelaceae Origin: Chemistry and Biology

Advances in Total Synthesis of Some 2,3,5‐Trisubstituted Tetrahydrofuran Natural Products

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