Stereoselective total synthesis of (+)-mueggelone, a novel inhibitor of fish development

Yadav, J. S.; Somaiah, R.; Kontham, Ravindar; Chandraiah, L.

doi:10.1016/j.tetlet.2008.02.022

Cited by 18 publications

(12 citation statements)

References 16 publications

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“…The synthesis of acid fragment 3 startedw ith 1,9-nonane diol (5), which was converted into epoxy alcohol 7 [11] through its correspondinga llylic alcohol by treatingw ith (À)-diisopropyld-tartrate (DIPT) in the presence of Ti(OiPr) 4 and tBuOOH as the oxidizing agent under Katsuki-Sharpless [12] conditions in 92 %y ield and with 97 % ee (Scheme 2). The epoxyalcohol 7 was convertedi nto its corresponding chloro derivative with CCl 4 in the presence of Ph 3 Pa nd NaHCO 3 followed by base-induced epoxide ring opening [13] with nBuLi at À78 8C, which furnished acetylenic alcohol 8 in 80 %y ield over two steps.…”

Section: Resultsmentioning

confidence: 99%

Total Synthesis of Sacrolide A by Following a Nozaki‐Hiyama‐Kishi Macrocyclization Strategy

2016

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Section: Resultsmentioning

confidence: 99%

Total Synthesis of Sacrolide A by Following a Nozaki‐Hiyama‐Kishi Macrocyclization Strategy

2016

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“…Its alcohol and carboxylic acid moieties can react under Yamaguchi conditions 29 to yield a 10-membered ring lactonization product, while the presence of the terminal double bond has been used for chain elongation via metathesis reaction 30 using Grubbs catalyst. Several compounds have been synthesized following these approaches including (+)-mueggelone, 31 an inhibitor of fish development as well as malyngic, fulgidic 32 , pinellic acids 33 and the botanical analogues of prostaglandins, phytoprostanes. 34 …”

Section: Discussionmentioning

confidence: 99%

“…The synthesis of one of the two enantiomers has been rather challenging often requiring several synthetic steps 31–34 despite recent advances using a chiral palladium catalyst. 35 The chirality of the active site of the P450 BM3 enzyme is well documented leading often exclusively to the R enantiomer for the monooxygenated long chain fatty acids.…”

Section: Discussionmentioning

confidence: 99%

Regio- and stereoselective hydroxylation of 10-undecenoic acid with a light-driven P450 BM3 biocatalyst yielding a valuable synthon for natural product synthesis

Kato

Nguyen

Gonzalez

et al. 2014

Bioorganic & Medicinal Chemistry

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We report herein the selective hydroxylation of 10-undecenoic acid with a light-activated hybrid P450 BM3 enzyme. Under previously developed photocatalytic reaction conditions, only a monohydroxylated product is detected by gas chromatography. Hydroxylation occurs exclusively at the allylic position as confirmed from a synthesized authentic standard. Investigation into the stereochemistry of the reaction indicates that the R enantiomer is obtained in 85% ee. The (R)-9-hydroxy-10-undecenoic acid obtained enzymatically is a valuable synthon en route to various natural products further expanding the light-activated P450 BM3 biocatalysis and highlighting the advantages over traditional methods.

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“…Generally, RCM and Yamaguchi lactonization are alternative and complementary ways for the synthesis of nonanolides [45,[102][103][104][105][106][107][108][109][110][111][112][113].…”

Section: Yamaguchi Lactonizationmentioning

confidence: 99%

Nonanolides of Natural Origin: Structure, Synthesis, and Biological Activity

Sun¹,

Lu²,

Ree³

et al. 2012

curr med chem

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Naturally occurring nonanolides (synonym decanolides) are a large family of secondary metabolites with an interesting 10- membered macrolide subunit. Metabolites of the nonanolide family have been found to have various biological activities, including cytotoxic, phytotoxic, antimalarial, antifungal, antibacterial, and antimicrofilament activities. An early review of the chemistry and bioactivity of nonanolides was presented in 1996, covering the literature published between 1975 and 1995. During the past decades, the broad spectrum of bioactivity and the intriguing structure of the medium-sized ring in nonanolide analogues have continuously drawn the attention of biologists and natural product and synthetic chemists, resulting in a great number of publications. This review summarizes in whole the recent progress in the field of the nonanolides of natural origin, aiming to give the readers a brief view of the compounds, concerning their natural occurrence, structural elucidation, biological activities, total synthesis, and structure-activity relationships. The article covers the literature published in the period from the beginning of 1996 to July 2011.

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Stereoselective total synthesis of (+)-mueggelone, a novel inhibitor of fish development

Cited by 18 publications

References 16 publications

Total Synthesis of Sacrolide A by Following a Nozaki‐Hiyama‐Kishi Macrocyclization Strategy

Total Synthesis of Sacrolide A by Following a Nozaki‐Hiyama‐Kishi Macrocyclization Strategy

Regio- and stereoselective hydroxylation of 10-undecenoic acid with a light-driven P450 BM3 biocatalyst yielding a valuable synthon for natural product synthesis

Nonanolides of Natural Origin: Structure, Synthesis, and Biological Activity

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