Catalytic Activity Studies of Aminocarbonyl Group Containing Hoveyda-Grubbs-Type Complexes for the Syntheses of Herbarumin I and Stagonolide A

Mohapatra, Debendra K.; Somaiah, R.; Rao, M. Mallikarjuna; Caïjo, Fréderic; Mauduit, Marc; Yadav, J. S.

doi:10.1055/s-0029-1219807

Cited by 26 publications

(12 citation statements)

References 5 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: 69%

“…4) was found to be superior to the Grubbs 1 st and 2 nd generation as well as the Hoveyda-Grubbs catalysts (Fig. 4) and suggesting novel stereoselectivity [79].…”

Section: First Selection Of the Ruthenium Catalyst For Rcm Is Importmentioning

confidence: 88%

“…Many total syntheses of nonanolides have been reported with the stereogenic centres derived from chiral pool starting materials, the majority of which are carbohydrates such as D-mannitol [47,77,78,127], D-glucose [79,81,128,129], D-ribose [61,64,88,130], L-arabinose [103], L-rhamnose, [47] and D-ribonolactone acetonide derivative [65,66]. Other chiral materials are also widely employed in asymmetric syntheses, for example, L-malic acid [97,113,123], Sor R-propylene oxide [46,48,92], the butane diacetal of glycolic acid (BDA) [67,68], and glyceraldehyde derivatives [83,93,113].…”

Section: Stereogenic Centres Derived From Chiral Pool Starting Materialsmentioning

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%

“…Finally, deprotection yielded herbarumin I(40). Selective oxidation of the allylic hydroxyl group in 40 gave stagonolide A (44)[79].Díez et al in 2003 reported the total synthesis of herbarumin II (41) using the butane diacetal (BDA) of glycolic acid as building block (Scheme 38). The starting material R,R-glycolate 292 was subjected to an aldol reaction with acrolein [Selvam's synthesis of herbarumin I (40) (2009).…”

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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: 69%

“…4) was found to be superior to the Grubbs 1 st and 2 nd generation as well as the Hoveyda-Grubbs catalysts (Fig. 4) and suggesting novel stereoselectivity [79].…”

Section: First Selection Of the Ruthenium Catalyst For Rcm Is Importmentioning

confidence: 88%

Section: Stereogenic Centres Derived From Chiral Pool Starting Materialsmentioning

confidence: 99%

Section: Examples Of Total Synthesismentioning

confidence: 99%

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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[1,3-Bis[2,6-bis(1-methyethyl)phenyl]-2-imidazolidinylidene]dichloro[[2-(1-methylethoxy-κO)-5[(2,2,2-trifluoroacetyl)amino]phenyl]methylene-κC]-Ruthenium

Caïjo¹,

Ret

Crévisy

et al. 2012

Encyclopedia of Reagents for Organic Synthesis

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Total Syntheses of Dendrodolides A, B, and E

et al. 2014

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Convergent total syntheses of dendrodolides A, B, and E comprising 12‐membered macrolactones are described. The syntheses of dendrodolides A and B were accomplished in 11 linear steps with 24 % and 25 % overall yield, respectively, starting from commercially available homoallyl alcohol 19 and enantiomerically pure epoxide 20. Dendrodolide E was subsequently obtained from dendrodolides A or B in 81 % yield by treatment with BCl3. Key steps were Maruoka asymmetric allylation, Corey‐Chaykovsky reaction, Yamaguchi esterification, and ring‐closing metathesis.

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Catalytic Activity Studies of Aminocarbonyl Group Containing Hoveyda-Grubbs-Type Complexes for the Syntheses of Herbarumin I and Stagonolide A

Cited by 26 publications

References 5 publications

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

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

[1,3-Bis[2,6-bis(1-methyethyl)phenyl]-2-imidazolidinylidene]dichloro[[2-(1-methylethoxy-κO)-5[(2,2,2-trifluoroacetyl)amino]phenyl]methylene-κC]-Ruthenium

Total Syntheses of Dendrodolides A, B, and E

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