Chemo-enzymatic asymmetric total synthesis of stagonolide-C

Jana, Nandan Kumar; Mahapatra, Tridib; Nanda, Samik

doi:10.1016/j.tetasy.2009.10.007

Cited by 51 publications

(18 citation statements)

References 28 publications

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“…As shown in Fig. 5, this assumption was well documented in the synthesis of multiplolide A [47], herbarumins [79,[81][82][83][84][85], stagonolides [61,[86][87][88], aspinolide A [89], achaetolide [51,90,91], and the antimalarial nonenolide [92].…”

Section: Second the Selection Of Protecting Groups To Be Attached Tomentioning

confidence: 73%

“…Introducing the chiral homoallylic alcohol or transforming to the required stereochemistry was often achieved by Keck asymmetric allylation [44,51,82,122,129] or by Mitsunobu inversion [84,87,91,104,116].…”

Section: Keck Asymmetric Allylation [135] and Mitsunobu Inversion [118]mentioning

confidence: 99%

“…The total syntheses of the herbarumins I-III (40)(41)(42) [65][66][67][68][69]77,79,[81][82][83][84][85][103][104][105]128,131,133,139], microcarpalide (43) [70][71][72][73][74][75]81,108,[140][141][142][143][144][145][146], the stagonolides (17)(18)(19)(20)(21)(22)(23) and (44)(45) [61,64,[86][87][88]…”

Section: Examples Of Total Synthesismentioning

confidence: 99%

“…Deprotection of the PMB group in 189 produced an alcohol, which was esterified with acid 180 prepared earlier in their lab. [87] The RCM reaction of ester 190 failed with Grubbs 1 st generation and 2 nd generation carbene complex. After removing the PMB group in 190, the resulting diene was subjected to RCM reaction with Grubbs 2 nd generation catalyst to furnish the stagonolide D (18) with E geometry [171].…”

mentioning

confidence: 99%

“…The Results of RCM-Mediated Construction of Some Nonanolides with and without Protecting Groups. synthesis of stagonolides A and C(44,17) and achaetolide(49) [87,91,130].…”

mentioning

confidence: 99%

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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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Section: Second the Selection Of Protecting Groups To Be Attached Tomentioning

confidence: 73%

Section: Keck Asymmetric Allylation [135] and Mitsunobu Inversion [118]mentioning

confidence: 99%

Section: Examples Of Total Synthesismentioning

confidence: 99%

mentioning

confidence: 99%

“…The Results of RCM-Mediated Construction of Some Nonanolides with and without Protecting Groups. synthesis of stagonolides A and C(44,17) and achaetolide(49) [87,91,130].…”

mentioning

confidence: 99%

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

Sun¹,

Lu²,

Ree³

et al. 2012

curr med chem

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Olefin Ring‐Closing Metathesis

Yet

2016

Organic Reactions

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The olefin ring‐closing metathesis reaction catalyzed by ruthenium and molybdenum complexes has been employed in the syntheses of carbocycles, heterocycles, supramolecular compounds, and in tandem metathesis reactions. Chiral ruthenium and molybdenum catalysts have provided high enantiomeric and diastereomeric excesses in ring‐closing metathesis reactions. Many of the unsuccessful medium‐ and large‐sized ring formations which were unsuccessful by traditional methods, such as the intramolecular Wittig, Horner–Wadsworth–Emmons, and Julia–Kocienski reactions, can now be formed by olefin ring‐closing metathesis reactions. Ring‐closing metathesis has been a key step and sometimes the only successful method for the synthesis of numerous natural products and drug discovery targets. The objective of this chapter is to provide an updated, comprehensive coverage of the literature of the olefin ring‐closing metathesis reaction and related processes. Key mechanistic points are summarized.

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Enzymatic Dynamic Kinetic Resolution in Stereoselective Synthesis

Rebolledo

González‐Sabín

Gotor

2013

Stereoselective Synthesis of Drugs and Natural Products

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The chemoenzymatic dynamic kinetic resolution (DKR) protocol combines the enzyme‐catalyzed resolution of a racemic substrate with the in situ racemization of the less reactive enantiomer, thus, producing optically active products in up to quantitative yield. This is of great interest for the pharmaceutical industry because by using this methodology, some of the serious drawbacks associated with drug production can be solved. Enzymatic DKRs are environmentally friendly processes that could help reduce cost and waste. The first and principal section of this chapter addresses the usefulness of hydrolases (particularly lipases) for the DKR of alcohols, diols, amines, and esters. In the following sections, DKRs with other enzymes such as haloalcohol dehalogenase, dehydrogenases, transaminases, and Baeyer‐Villiger monooxygenases are considered.

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Chemo-enzymatic asymmetric total synthesis of stagonolide-C

Cited by 51 publications

References 28 publications

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

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

Olefin Ring‐Closing Metathesis

Enzymatic Dynamic Kinetic Resolution in Stereoselective Synthesis

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