1,1‐Divinylallene

Cergol, Katie M.; Newton, Christopher G.; Lawrence, Andrew L.; Willis, Anthony C.; Paddon‐Row, Michael N.; Sherburn, Michael S.

doi:10.1002/anie.201105541

Cited by 28 publications

(23 citation statements)

References 45 publications

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“…Indigenous women also have higher rates of other sexually transmitted infections (STIs) [10], and an earlier age at first sexual intercourse[30]. More Indigenous women also live in poverty [19,31], and greater persistence of HPV due to failure of immunological control could be in part attributable to the effects of lower socioeconomic status or general health status, in combination with high rates of smoking, earlier and more pregnancies, and the presence of other STIs. It could also reflect poorer access to cervical cytology screening by Indigenous women in this age group: this has been hypothesized to be an important factor in the higher rates of cervical cancer incidence and mortality observed in Indigenous women [21,32].…”

Section: Discussionmentioning

confidence: 99%

Human papillomavirus prevalence among indigenous and non-indigenous Australian women prior to a national HPV vaccination program

Garland

Brotherton

Condon

et al. 2011

BMC Med

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BackgroundIndigenous women in Australia have a disproportionate burden of cervical cancer despite a national cervical screening program. Prior to introduction of a national human papilloma virus (HPV) vaccination program, we determined HPV genotype prevalence by Indigenous status and residence in remote areas.MethodsWe recruited women aged 17 to 40 years presenting to community-based primary health services for routine Pap screening across Australia. A liquid-based cytology (LBC) cervical specimen was tested for HPV DNA using the AMPLICOR HPV-DNA test and a PGMY09/11-based HPV consensus PCR; positive specimens were typed by reverse hybridization. We calculated age-adjusted prevalence by weighting to relevant population data, and determined predictors of HPV-DNA positivity by age, Indigenous status and area of residence using logistic regression.ResultsOf 2152 women (655 Indigenous), prevalence of the high-risk HPV genotypes was similar for Indigenous and non-Indigenous women (HPV 16 was 9.4% and 10.5%, respectively; HPV 18 was 4.1% and 3.8%, respectively), and did not differ by age group. In younger age groups, the prevalence of other genotypes also did not differ, but in those aged 31 to 40 years, HPV prevalence was higher for Indigenous women (35% versus 22.5%; P < 0.001), specifically HPV clades α5 (OR = 2.1, 95% CI 1.1 to 4.3) and α7, excluding type 18 (OR 1.9, 95% CI 1.1 to 3.3). In multivariate analysis, detection of any HPV genotype was strongly associated with smoking and Pap-test abnormalities, with both risk factors more common among Indigenous women.ConclusionAlthough we found no difference in the prevalence of HPV16/18 among Australian women by Indigenous status or, for Indigenous women, residence in remote regions, differences were found in the prevalence of risk factors and some other HPV genotypes. This reinforces the importance of cervical screening as a complement to vaccination for all women, and the value of baseline data on HPV genotype prevalence by Indigenous status and residence for the monitoring of vaccine impact.

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Section: Discussionmentioning

confidence: 99%

Human papillomavirus prevalence among indigenous and non-indigenous Australian women prior to a national HPV vaccination program

Garland

Brotherton

Condon

et al. 2011

BMC Med

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“…Our recent successful preparation of the parent 1,1-divinylallene revealed the hydrocarbon's susceptibility to DA polymerization, a characteristic that, in combination with the low boiling point of the substance, dictated a somewhat lengthy synthesis 20 . We ventured that chiral trimethyl analogue 6 would be both less volatile and less prone to self-immolation than its parent, and consequently set about its synthesis in a significantly more direct manner (Fig.…”

Section: Resultsmentioning

confidence: 99%

Pseudopterosin synthesis from a chiral cross-conjugated hydrocarbon through a series of cycloadditions

et al. 2014

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The pseudopterosins are a family of diterpene marine natural products, which, by virtue of their interesting anti-inflammatory and analgesic properties, have attracted the attentions of many synthetic chemists. The most efficient syntheses reported to date are 14 and 20 steps in the longest linear sequence for chiral pool and enantioselective approaches, respectively, and all start with precursors that are easily mapped onto the natural product structure. Here, we describe an unconventional approach in which a chiral cross-conjugated hydrocarbon is used as the starting material for a series of three cycloadditions. Our approach has led to a significant reduction in the step count required to access these interesting natural products (10 steps chiral pool and 11 steps enantioselective). Furthermore it demonstrates that cross-conjugated hydrocarbons, erroneously considered by many to be too unstable and difficult to handle, are viable precursors for natural product synthesis.

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“…This π-bond rich hydrocarbon was prepared and characterized by our research group for the first time in 2011 [30]. The hydrocarbon undergoes a diene-transmissive sequence of three Diels-Alder reactions using N-phenylmaleimide as the dienophile (Scheme 17).…”

Section: Applications Of the Dendralenes In Synthesismentioning

confidence: 99%

Demystifying the dendralenes

Mackay

Sherburn

2013

Pure and Applied Chemistry

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We present herein an overview of our ongoing studies with dendralenes. The first synthetic routes to this fundamental family of compounds have revealed long-hidden secrets in hydrocarbon chemistry and set the scene for synthetic and materials chemistry applications.While we have had significant success in the functionalization and reactions of the dendralenes, we have occasionally encountered selectivity issues. In an effort to gain more control over the reactivity of the dendralenes, we turned to iron tricarbonyl complexes as 1,3-butadiene masking groups [19]. For example, we found that [3]dendralene can be converted into iron tricarbonyl complex 41 in good yield (Scheme 9). Treatment of the iron complex 41 with ceric ammonium nitrate (CAN) resulted in decomplexation and high-yielding recovery of the hydrocarbon.This complexation allows selective mono-1,3-dipolar cycloaddition, as well as mono-cyclopropanation and -dihydroxylation, feats that had proved unattainable on the parent dendralene [19] (Scheme 10). This gave us an array of functionalized 1,3-butadienes 44, 45, and 46 in complexed form, which could be decomplexed and reacted further. Cross-metathesis reactions allowed a very straightforward synthesis of substituted dendralenes 47 (in complexed form), and self-metathesis of the iron tricarbonyl complex of [3]dendralene generated compound 48. Decomplexation with CAN allowed the first synthesis of pentaene 49, one of the simplest possible structures containing both through-and cross-conjugation.

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1,1‐Divinylallene

Cited by 28 publications

References 45 publications

Human papillomavirus prevalence among indigenous and non-indigenous Australian women prior to a national HPV vaccination program

Human papillomavirus prevalence among indigenous and non-indigenous Australian women prior to a national HPV vaccination program

Pseudopterosin synthesis from a chiral cross-conjugated hydrocarbon through a series of cycloadditions

Demystifying the dendralenes

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