Total synthesis of (+)-petromyroxol

Mullapudi, Venkannababu; Ramana, Chepuri V.

doi:10.1016/j.tetlet.2015.04.129

Cited by 10 publications

(5 citation statements)

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“…Mullapudi and Ramana [88] (2015) displayed a straight forward synthesis of (+)-petromyroxol and its three diastereom-ers from commercially available D-glucose 134 (Scheme 33). The epoxide 135 was synthesized from D-glucose in 7 steps.…”

Section: Total Synthesis Of (+)-Petromyroxol (4)mentioning

confidence: 99%

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

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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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Section: Total Synthesis Of (+)-Petromyroxol (4)mentioning

confidence: 99%

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

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Pathare

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2020

Chemistry An Asian Journal

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“…In parallel to the report of Boyer, we reported the synthesis of 1 along with three possible diastereomers. 11 Interestingly, one of the diastereomers was found to be (−)- iso -petromyroxol ( 2 ), 9 the isolation of which appeared at the same time. In this manuscript, we document the complete details of the total synthesis of 1 and 2 along with the other six possible diastereomers and their NMR characterization details.…”

Section: Introductionmentioning

confidence: 99%

“… 10 Subsequently, four more total syntheses of (+)-petromyroxol ( 1 ) have been documented. 11 − 14 Immediately after the report on the isolation of 1 and its enantiomer, we initiated its total synthesis. In general, considering the presence of four stereogenic centers present in petromyroxol 1 , there exists the possibility of eight enantiomeric pairs.…”

Section: Introductionmentioning

confidence: 99%

“…The simple/unique structures of these compounds, as well as their promising olfactory activity against sea lamprey, have led to them attracting the attention of the synthetic community. − The first total synthesis of (+)-petromyroxol ( 1 ) was executed single-handedly by Boyer . Subsequently, four more total syntheses of (+)-petromyroxol ( 1 ) have been documented. − Immediately after the report on the isolation of 1 and its enantiomer, we initiated its total synthesis.…”

Section: Introductionmentioning

confidence: 99%

“…Keeping this in mind, and considering the ready availability of C5-epimeric epoxides 5 and 5′ , we planned the synthesis of 1 along with all of the possible seven isomers (Figure ). In parallel to the report of Boyer, we reported the synthesis of 1 along with three possible diastereomers . Interestingly, one of the diastereomers was found to be (−)- iso -petromyroxol ( 2 ), the isolation of which appeared at the same time.…”

Section: Introductionmentioning

confidence: 99%

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Total Synthesis of (+)-Petromyroxol, (−)-iso-Petromyroxol, and Possible Diastereomers

et al. 2020

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The total synthesis of (+)-petromyroxol ( 1 ) and its seven diastereomers including the (−)- iso -petromyroxol ( 2 ) is described. The employed strategy involves the use of easily available C5-epimeric epoxides 5 and 5′ and nonselective anomeric C1-allylation, proceeding with or without inversion at C2, thereby giving the possibility of synthesizing all possible diastereomers. Extensive two-dimensional (2D) NMR analyses of all eight diastereomers have been carried out to assign the chemical shifts of the central carbons and the corresponding attached hydrogens and to learn how the C/H-chemical shifts of the tetrahydrofuran ring were influenced by the adjacent centers.

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Total Synthesis of (+)‐Petromyroxol, a Marine Natural Product

2015

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in recognition of his seminal contributionst os omany aspects of organicchemistry.Abstract: An efficient total synthesis of (+ +)-petromyroxol, am arine naturalp roduct, is described. The synthesisu tilizes the Sharpless asymmetric dihydroxylation (AD), intramolecular S N 2c yclization and stereoselective Grignard reaction as key steps.The 2,5-disubstituted-3-oxygenated THF motif is found abundantly in biologically active natural products. [1] Petromyroxol (1), iso-petromyroxol (2), [2] trans-(À)-kumausyne( 3), trans-(+ +)-deacetylkumausyne (4), [3] and anthelmintic oxylipid( 5), [4] marine natural products, are few examples of dihydroxytetrahydrofurans from the acetogenin family [5] (Figure 1).The dihydroxylated THF enantiomers( + +)-petromyroxol [2a] and iso-petromyroxol [2b] were recently isolated by Li and coworkers from water conditioned with larvae of the sea lamprey, Petromyzon marinus L.,w hich is the first example of dihydroxylated THF-containingm etabolites isolated from av ertebrate. [2]

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Total synthesis of (+)-petromyroxol

Cited by 10 publications

References 36 publications

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

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

Total Synthesis of (+)-Petromyroxol, (−)-iso-Petromyroxol, and Possible Diastereomers

Total Synthesis of (+)‐Petromyroxol, a Marine Natural Product

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