Total Synthesis and Determination of Relative and Absolute Configuration of Multiplolide A

Ramana, Chepuri V.; Khaladkar, Tushar P.; Chatterjee, Snigdhansu; Gurjar, Mukund K.

doi:10.1021/jo7027568

Cited by 33 publications

(19 citation statements)

References 38 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%

“…The presence of a conformational equilibrium (3.5:1) was observed in the NMR spectrum of 43 recorded in CD 3 CN [25]. Phomolides A and B (46,47), two nonanolides containing a propyl unit at C-9, were isolated from the culture of Phomopsis sp. hzla01-1.…”

Section: Nonanolides With Extended Alkyl Chainsmentioning

confidence: 97%

“…NMR spectroscopy in combination with X-ray crystal structure analyses, Mosher's method, [ ] D values, CD, or quantum chemical CD calculations were extensively used in the elucidation of the relative and absolute configurations of nonanolides. In some cases, the absolute stereochemistry of nonanolides, for example putaminoxin (35) [44], mueggelone (39) [45], sporostatin (53) [46], multiplolide A (4) [47], xestodecalactones A, B and C (54)(55)(56) [48][49][50], and achaetolide (49) [41,51] were established by stereoselective total synthesis. The nonanolide class of metabolites is classified according to the previously established criteria: (i) simple nonanolides with methyl and oxygen substituents (Fig.…”

Section: Structures and Classification Of Nonano-lidesmentioning

confidence: 99%

“…Fungicolous fungus [36] 8a-Acetoxy-5a-hydroxy-7-oxodecan-9-olide (31) 7a-Acetoxymultiplolide A (32) 8a-Acetoxymultiplolide A (33) Phomopsis sp. YM 311483 Endophytic fungus [37] Phomolides A, B (46,47) Phomopsis sp. Hzla01-1 Marine-derived fungus [38] Phomolide C (61) Phomopsis sp.…”

Section: Simple Nonanolides With Methyl and Oxygen Substituentsmentioning

confidence: 99%

“…Multiplolides A and B (4,5) were isolated from the broth extract of the fungus Xylaria multiplex BCC 1111 with their structures being deduced from the spectral data. The absolute configurations of both compounds were solved by Mosher's method, except the orientation of the epoxide ring [26], which was later established by a total synthesis [47]. Bioassay directed fractionations led to isolation of pollen growth regulators fusanolides A and B (6, 7) from the fungus Fusarium sp.…”

Section: Simple Nonanolides With Methyl and Oxygen Substituentsmentioning

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: Nonanolides With Extended Alkyl Chainsmentioning

confidence: 97%

Section: Structures and Classification Of Nonano-lidesmentioning

confidence: 99%

Section: Simple Nonanolides With Methyl and Oxygen Substituentsmentioning

confidence: 99%

Section: Simple Nonanolides With Methyl and Oxygen Substituentsmentioning

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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