Total synthesis of (+)-jatropholone A and B

Smith, Amos B.; Liverton, Nigel J.; Hrib, Nicholas J.; Sivaramakrishnan, H.; Winzenberg, Kevin N.

doi:10.1021/jo00217a054

Cited by 24 publications

(18 citation statements)

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“…Our accumulation of interests and efforts in anion chemistry 17,20,32–34 led to the discovery and validation of a two-component indole construction tactic (Scheme 6) which was initiated by bis-metalation of an N-silyl- o -toluidine. 35 The resulting dianion was then added to an ester to generate the corresponding ketone, which in turn would undergo an intramolecular aza-Peterson olefination/tautomerization to yield the disubstituted indole in a “single flask”.…”

Section: Discussionmentioning

confidence: 99%

Total synthesis of architecturally complex indole terpenoids: strategic and tactical evolution

Zou

Smith

2017

J Antibiot

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Section: Discussionmentioning

confidence: 99%

Total synthesis of architecturally complex indole terpenoids: strategic and tactical evolution

Zou

Smith

2017

J Antibiot

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“…As in Smith’s classic synthesis of jatropholone A ( 27 ) (Figure 2), the identification and exploitation of a dimethylcyclopropane-containing chiral pool terpene was highly simplifying. 39 This work also highlights how judicious retrosynthetic planning, in conjunction with two highly powerful metathesis-based events, 279 can be leveraged in the construction of topologically and thermodynamically challenging polycyclic ring systems.…”

Section: Syntheses From the 21st Centurymentioning

confidence: 95%

“…38 Similarly, jatropholone A ( 27 ) does not contain the carbon skeleton of (−)-carene, but its dimethylcyclopropane unit is suggestive of this unique monoterpene and this recognition was leveraged by Smith in a concise total synthesis of this compound. 39 …”

Section: Starting Points and Historical Perspectivementioning

confidence: 99%

“…Wender and co-workers exploited this similarity in their pioneering synthesis of 26 from carvone wherein a C–C bond of carvone was ultimately broken . Similarly, jatropholone A ( 27 ) does not contain the carbon skeleton of (−)-carene, but its dimethylcyclopropane unit is suggestive of this unique monoterpene and this recognition was leveraged by Smith in a concise total synthesis of this compound …”

Section: Starting Points and Historical Perspectivementioning

confidence: 99%

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Navigating the Chiral Pool in the Total Synthesis of Complex Terpene Natural Products

et al. 2017

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The pool of abundant chiral terpene building blocks (i.e. “chiral pool terpenes”) has long served as a starting point for the chemical synthesis of complex natural products, including many terpenes themselves. As inexpensive and versatile starting materials, such compounds continue to influence modern synthetic chemistry. This review highlights 21st century terpene total syntheses which themselves use small, terpene-derived materials as building blocks. An outlook to the future of research in this area is highlighted as well.

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“…In general practice, the size and shape of the 555 sorting block can be varied in three dimensions as ∆L*, ∆a* and ∆b* tolerances, in order to yield an optimum condition for shade sorting. Smith published a reference guideline to set these tolerances [11]. However, it is unclear whether this calculation has ever been done or not.…”

Section: Background To Shade Sortingmentioning

confidence: 99%

Regression analysis to determine the optimum colour tolerance level for instrumental shade sorting

Yuen

Yeung

et al. 1999

Coloration Technology

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An investigation of the correlation between visual colour assessment and instrumental colour acceptance determination using regression analysis has been carried out. Three colour‐difference equations, CIELAB, CMC(2:1) and CIE94(2:1:1), were studied in order to determine which is the best for generating a uniform colour space/microspace for allocating the colour population in shade sorting. Determination of optimum colour tolerance for further shade sorting was also undertaken. Some 1320 pairs of dyed samples distributing around 20 shade standards were measured instrumentally and also evaluated visually by a panel of 32 observers. Percentage rejection was plotted against colour difference and different mathematical regression relationships were then imposed. As a result, both CMC and CIE94 showed better correlation between the two colour assessment methods than the CIELAB colour‐difference equation. Consequently, optimum colour tolerance limits were determined for subsequent development of shade sorting, with the findings being equally applicable to colour acceptance (shade passing).

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Total synthesis of (+)-jatropholone A and B

Cited by 24 publications

References 0 publications

Total synthesis of architecturally complex indole terpenoids: strategic and tactical evolution

Total synthesis of architecturally complex indole terpenoids: strategic and tactical evolution

Navigating the Chiral Pool in the Total Synthesis of Complex Terpene Natural Products

Regression analysis to determine the optimum colour tolerance level for instrumental shade sorting

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