Effect of the allylic substituents on ring closing metathesis: the total synthesis of stagonolide B and 4-epi-stagonolide B

Giri, Awadut G.; Mondal, Mohabul A.; Puranik, Vedavati G.; Ramana, Chepuri V.

doi:10.1039/b916198h

Cited by 35 publications

(13 citation statements)

References 48 publications

(27 reference statements)

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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: 91%

“…The outcome of this reaction is sensitive to many factors, such as structure of substrates, the nature of the catalyst, and the steric crowding around the newly forming ring olefin [61]. Some possible factors influencing E/Z selectivity and reactivity are discussed here.…”

Section: Ring Closing Metathesis (Rcm)mentioning

confidence: 97%

“…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%

“…Coupling the acid S-172 and alcohol 156 afforded the diene epi-175. The RCM of the fully protected epi-175 was facile with 2 nd generation Grubbs catalyst to give 4-epi-45 [61].…”

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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: 91%

Section: Ring Closing Metathesis (Rcm)mentioning

confidence: 97%

Section: Stereogenic Centres Derived From Chiral Pool Starting Materialsmentioning

confidence: 99%

Section: Examples Of Total Synthesismentioning

confidence: 99%

“…Coupling the acid S-172 and alcohol 156 afforded the diene epi-175. The RCM of the fully protected epi-175 was facile with 2 nd generation Grubbs catalyst to give 4-epi-45 [61].…”

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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