EBC‐219: A New Diterpene Skeleton, Crotinsulidane, from the Australian Rainforest Containing a Bridgehead Double Bond

Maslovskaya, Lidiya A.; Savchenko, Andrei I.; Krenske, Elizabeth H.; Pierce, Carly J.; Gordon, Victoria; Reddell, Paul; Parsons, Peter G.; Williams, Craig M.

doi:10.1002/ange.201310923

Cited by 14 publications

(3 citation statements)

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“…The solitary entry in this section was discovered only very recently by Reddell, Parsons, and Williams in the stems of Croton insularis (Baill) in a campaign aimed at discovering new anti-cancer agents from the Australian rainforest, in collaboration with EcoBiotics Ltd. [16] The structure of the bicyclo[10.2.1]pentadec-2,6,13-triene ring system of EBC-219 (137; Scheme 8) was determined by NMR spectroscopy, specifically through the observation of key HMBC correlations. DFT calculations indicated that four low-energy conformations could be adopted by the macrocyclic ring system.…”

Section: 1] Systemsmentioning

confidence: 99%

“…[15] Furthermore, and perhaps even more importantly, we had recently isolated a novel natural product that contained a bridgehead double bond, and therefore wanted to better understand the application of Bredts rule to natural product systems. [16] In consideration of the above and the fact that it was Bredts century-old work on the camphene and pinane natural product series that resulted in the formulation of the rule, it seemed fitting to review this special class of natural products for the first time.…”

Section: Introductionmentioning

confidence: 99%

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Natural Products with Anti‐Bredt and Bridgehead Double Bonds

2014

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Well over a hundred years ago, Professor Julius Bredt embarked on a career pursuing and critiquing bridged bicyclic systems that contained ring strain induced by the presence of a bridgehead olefin. These endeavors founded what we now know as Bredt's rule (Bredtsche Regel). Physical, theoretical, and synthetic organic chemists have intensely studied this premise, pushing the boundaries of such systems to arrive at a better understood physical phenomenon. Mother nature has also seen fit to construct molecules containing bridgehead double bonds that encompass Bredt's rule. For the first time, this topic is reviewed in a natural product context.

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Section: 1] Systemsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Natural Products with Anti‐Bredt and Bridgehead Double Bonds

2014

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“…This method unequivocally predicts all known natural products having bridgehead double bonds to be ''isolable,'' providing a powerful tool for assignment of natural products containing bridgehead double bonds. 28 Since it first emerged in the 1980s, hundreds of natural products with a bridgehead double bond have been isolated by the phytochemists, such as the famous taxol, CP molecules, the newly identified EBC-219, 29 mangelonoid A, 30 brassicicene M, 31 schiglautone A, 32 and others [33][34][35][36][37] (Figure 2). Due to their noticeable complexity, with different ring strain energy in the skeleton (Fawcett's S value highlighted in blue in Figure 2), and promising bioactivity, these natural products have attracted considerable research attention and large sections of them have been synthesized using different strategies.…”

Section: Introductionmentioning

confidence: 99%

Total Synthesis of Natural Products Containing a Bridgehead Double Bond

Liu

et al. 2020

Chem

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Natural products with a bridgehead double bond, such as taxol and CP molecules, have long attracted considerable attention from chemists because of their promising bioactivity and structural complexity, with the high ring-strain energy in the ring systems representing a formidable synthetic challenge. Herein, strategies for the total synthesis of such complex natural products are reviewed for the first time by using 26 representative studies. Methods for constructing the bridged ring system and bridgehead double bond have been emphasized, including syntheses of the same natural product by different research groups using different strategies, to showcase the diversity of thought and creativity in this area. The total synthesis of these natural products not only provides precious bioactive substances and promising candidates for drug discovery but also has stimulated incredible advances in the development of new strategies and synthetic methods.

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Naturstoffe mit Anti‐Bredt‐ und Brückenkopf‐Doppelbindung

2014

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Vor über hundert Jahren begann Professor Julius Bredt seine Forschungskarriere auf dem Gebiet der verbrückten bicyclischen Systeme, die durch ein Brückenkopf‐Alken unter Ringspannung stehen. Seine kritischen Betrachtungen mündeten in der Formulierung dessen, was wir heute als die Bredtsche Regel kennen. Seitdem versuchen Physikochemiker, Theoretiker und Synthesechemiker gleichermaßen, die Grenzen dieses physikalische Phänomens auszuloten, um es besser kennenzulernen. Der Bauplan der Natur sieht durchaus Brückenkopf‐Doppelbindungen nach der Bredtschen Regel vor. In diesem Aufsatz wird erstmals die Anwendung der Bredtschen Regel auf Naturstoffe umfassend erörtert.

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EBC‐219: A New Diterpene Skeleton, Crotinsulidane, from the Australian Rainforest Containing a Bridgehead Double Bond

Cited by 14 publications

References 50 publications

Natural Products with Anti‐Bredt and Bridgehead Double Bonds

Natural Products with Anti‐Bredt and Bridgehead Double Bonds

Total Synthesis of Natural Products Containing a Bridgehead Double Bond

Naturstoffe mit Anti‐Bredt‐ und Brückenkopf‐Doppelbindung

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