Progress in the Synthesis of Guanacastepenes

Mischne, Mirta P.

doi:10.2174/1570179053545350

Cited by 11 publications

(12 citation statements)

References 35 publications

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“…21 achievements in the total synthesis of guanacastepenes and heptemerones published aer 2006 are discussed. The work reported earlier was summarized in previous reviews 15, [18][19][20][21] and is briey reported here (vide supra).…”

Section: Introductionmentioning

confidence: 69%

“…In 2005, Sterner and co-workers isolated and characterised seven new neodolastanes, named heptemerones A-G (17)(18)(19)(20)(21)(22)(23). 24 The heptemerone family exhibited the same C8-and C11-congurations as reported for the guanacastepenes, although only the relative congurations were determined (the same numbering as for the neodolastane skeleton (1)).…”

Section: Structural Diversity Of Neodolastanesmentioning

confidence: 99%

“…15 In particular, neodolastanes, a structurally diverse family of 44 diterpenoids which includes guanacastepenes, heptemerones, plicatilisins, radianspenes, 2,15-epoxy-5,13-dihydroxyneodolast-3-en-14-one and sphaerostanol, 16,17 have inspired numerous synthetic research groups. The studies towards their syntheses were the subject of Mischne's (2005), 18 Hierseman's (2005 & 2006), 15,19 and Lee's (2006), 20 reviews. The excellent review by Baran (2007) on the modern synthesis of biologically active terpenoids also briey addresses the synthesis of guanacastepenes.…”

Section: Introductionmentioning

confidence: 99%

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The isolation and synthesis of neodolastane diterpenoids

et al. 2015

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The neodolastane diterpenoids comprise a group of 44 compounds including guanacastepenes, heptemerones, plicatilisins, radianspenes, 2,15-epoxy-5,13-dihydroxyneodolast-3-en-14-one and sphaerostanol. These fungal and marine natural products are characterized by a tricyclic neodolastane skeleton that consists of fused five-, seven- and six-membered rings. Their reported antibiotic activities against antibiotic-resistant bacteria together with strong antifungal and anticancer activities and their novel structures render these compounds interesting synthetic targets. The aim of this account is to summarise the progress in the isolation, characterisation and synthesis of these diterpenoids as well as to review their biogenetic origins and diverse biological activities since their discovery in 2000.

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Section: Introductionmentioning

confidence: 69%

Section: Structural Diversity Of Neodolastanesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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The isolation and synthesis of neodolastane diterpenoids

et al. 2015

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“…49) Guanacastepenes have attracted the interest of synthetic chemists around the world due to their unique structural features, which include two ring-junction quaternary methyl groups and a 5-7-6 tricyclic carbon skeleton [50][51][52][53] (Chart 17). This family also shows excellent activity against methicillin-resistant Staphylococcus aureas (MRSA) and vancomycin-resistant Enterococcus faecalis (VREF) pathogens.…”

Section: )mentioning

confidence: 99%

Development of Novel Cyclizations <i>via</i> Rhodacycle Intermediate and Its Application to Synthetic Organic Chemistry

Oonishi

2015

Chem. Pharm. Bull.

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Novel Rh(I)-catalyzed cyclizations through a different type of rhodacycle intermediate which is formedby hydroacylation of 4,6-dienal or oxidative addition of diene and alkene are described. Hydroacylation of 4,6-dienal afforded various 7-membered rings in good to high yields, while cycloisomerization of diene and alkene provided 5-or 6-membered rings in good yields. On the basis of these studies, we have also succeeded in developing the sequential reaction of hydroacylation followed by cycloisomerization to produce bicyclic compounds in a stereoselective manner and thus this reaction was expanded to the synthesis of epiglobulol. Furthermore, both Rh(I)-catalyzed hydroacylation and cycloisomerization using ionic liquid (IL) as a solvent were investigated and it was found that the IL recovered after the reaction, which contains the Rh(I) catalyst, could be recycled several times without loss of catalytic activity.

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“…6 Specifically, the challenges intrinsic to a total synthesis of guanacastepene A include an unprecedented 5-7-6 carbon framework bearing a dense array of oxygen and unsaturated functionalities opposite two ring junction quaternary methyl groups. In 2002, Danishefsky and co-workers reported the first total synthesis of guanacastepene A from a late-stage acetonide 1 (Figure 2).…”

Section: An Overview Of Synthetic Strategiesmentioning

confidence: 99%

Progress toward the Total Synthesis of Guanacastepene A

Maifeld¹,

Lee²

2006

Synlett

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P r o g r e s s t o w a r d t h eAbstract: Guanacastepene A, the leading member of a structurally diverse family of diterpene natural products, was isolated from the extracts of an unidentified fungus. The discovery of its potent antibiotic activity as well as its previously unreported tricyclic architecture render guanacastepene A an attractive and formidable target for total synthesis. Specifically, guanacastepene A's synthetic challenges include 2 ring-junction quaternary methyl groups and a novel 5-7-6 tricyclic carbon skeleton possessing a dense array of oxygen and unsaturated functionalities. In this account, we will discuss our motivation and efforts toward the total synthesis of guanacastepene A as well as highlight the contributions from the synthetic community toward this pursuit.

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Progress in the Synthesis of Guanacastepenes

Cited by 11 publications

References 35 publications

The isolation and synthesis of neodolastane diterpenoids

The isolation and synthesis of neodolastane diterpenoids

Development of Novel Cyclizations <i>via</i> Rhodacycle Intermediate and Its Application to Synthetic Organic Chemistry

Progress toward the Total Synthesis of Guanacastepene A

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