Интересные отрывки из The Way of Synthesis
Список далеко не полный, но эти захотелось выписать.
"In 1974 R. V. Stevens ... urged us not to confine our thoughts to any single representation of a molecule. ...view the target from all possible angles to avoid being limited by the view most often presented in literature."
"Any skill not passed on to three successive generations (in this case a "PhD generation" of four to six years) is lost and forgotten and must be reinvented in the future."
"To learn by example is to submit to authority. You follow your master because you trust his manner of doing things even when you cannot analyse and account in detail for its effectiveness. By watching the master and emulating his efforts in the presence of his example, the apprentice unconciously picks up the rules of the art, including those which are not explicitly known to the master himself (M. Polanyi)"
"A study conducted by NCI identified about 100 000 chemists whose citations for the period 1981-1996 exceeded a total of 500".
"Nothing has had a more negative effect on the credibility of synthesis than the taxol problem."
"Yield optimization should be first attended in the range 50-80%, rather than in the range 80-95%, because of the lower value of the improvement-to-effort ratio in the latter case"."
[оптимизируйте выход до 80%+ и сразу двигайтесь дальше]
"Hydroboration of carboxylic acids and alkynes is faster than of anything else. Acyl chlorides and aldehydes are essentially unreactive towards BH3."
"I was a postdoctoral associate with the late Wolfgand Oppolzer from 1977 to 1978. After I arrived in Geneva in August, I met Professor Oppolzer on the first Monday morning to dicsuss research. He handed me a three-by-five card with a total synthesis penciled on it and advised me that "there should be no reason not to publish this work before Christmas."
[прим.: полнейшее пренебрежение интеллектом своих рабочих и сведение их к простым "операторам колб"]
"I ran hundreds of reactions between August and December 1977. Professor Oppolzer was unconvinced that the problem was chemistry and not the operator and made frequent comments about "the technique of present-day American postdocs".
"Living in a department where a senior colleague (Bruce Rickborn) insisted that he did not believe in orbitals, made it difficult to maintain my stance."
[и это в конце 70-х годов!]
"At that time, only rudimentary research facilities and limited access to chemicals were available to us and such conditions of deprivation invariably propel one to think harder, to innovate and improvise"
[ну да, конечно. То-то Украина такая инновационная страна, что аж дух захватывает. С импровизацией согласен: из говна и палок мы можем слепить условно работающую лабораторию. Думаю, наличие посильных препятствий действительно способно стимулировать рост, как у спортсменов, что приседают со штангой. Но чересчур большие проблемы будут непреодолимы и переломают человека (опять таки, как слишком тяжелая штанга для новичка).]
"In addition, the chemical total synthesis of taxol represents a formidable milestone in the art and craft of organic synthesis − perhaps even an end to an era of total synthesis."
"The history of alkaloid chemistry precedes even the synthesis of urea by Wohler in 1828. Morphine, one of the most famous alkaloids, was isolated by Serturner in 1806."
"The publication of this manuscript was not without problems. It was originally submitted to Tetrahedron Letters and was rejected on the basis of ""unimportance of reprinting NMR data". It was accepted in Synthetic Communications after the argument was made that the literature has been very vague with respect to accurate experimental and spectral details. When it appeared, I received a letter from a very well-known senior chemist, previously active in this area, who complained bitterly that allusions made in the paper to the lack of spectral details were unnecessary and insulting. Of course, this partucular author did not report either physical or spectral properties of supinidine in his publication, only an unrealistically high yield obtained in his synthesis. I pointed out that if orgnaic chemists performed their task properly there would have been no need for our publication."
"Neither of us thought we were that lucky - and in fact the first attempt to deprotect the tosyo amide gave a mixture. However, Demos had an NMR spectrum of morphine that he had aquired as authentic material - just in case we ever got to the end. Demos [the student] could see the distinctive patterns of protons on the rigid morphine pentacycle in the NMR of his mixture."
"...accidental discoveries are meritorious only upon careful observation and analysis of the «accidents»."
"In an age in which there is very severe competition in reaching heights of absurdity in remarks, that comes pretty near taking the blue ribbon" - Woodward.
"The benefits of total synthesis as a means of access to important materials may be questioned in terms of overall effectiveness; however, there is, unquestionably, no better way to train synthetic organic chemists than through a long and arduous total synthesis."
[Полностью согласен с этим утверждением, если по химиком-органиком понимать "работник у станка вытяжки"]
"... Woodward's second generation synthesis of reserpine intermediate, Wender's cedrene synthesis, Heathcock's lycopodine and daphnilactone designs, Majetich's perovskone cascade, and the Merck indinavir synthesis seem very close to the limits of creative design and perfect execution."
"In 1974 R. V. Stevens ... urged us not to confine our thoughts to any single representation of a molecule. ...view the target from all possible angles to avoid being limited by the view most often presented in literature."
"Any skill not passed on to three successive generations (in this case a "PhD generation" of four to six years) is lost and forgotten and must be reinvented in the future."
"To learn by example is to submit to authority. You follow your master because you trust his manner of doing things even when you cannot analyse and account in detail for its effectiveness. By watching the master and emulating his efforts in the presence of his example, the apprentice unconciously picks up the rules of the art, including those which are not explicitly known to the master himself (M. Polanyi)"
"A study conducted by NCI identified about 100 000 chemists whose citations for the period 1981-1996 exceeded a total of 500".
"Nothing has had a more negative effect on the credibility of synthesis than the taxol problem."
"Yield optimization should be first attended in the range 50-80%, rather than in the range 80-95%, because of the lower value of the improvement-to-effort ratio in the latter case"."
[оптимизируйте выход до 80%+ и сразу двигайтесь дальше]
"Hydroboration of carboxylic acids and alkynes is faster than of anything else. Acyl chlorides and aldehydes are essentially unreactive towards BH3."
"I was a postdoctoral associate with the late Wolfgand Oppolzer from 1977 to 1978. After I arrived in Geneva in August, I met Professor Oppolzer on the first Monday morning to dicsuss research. He handed me a three-by-five card with a total synthesis penciled on it and advised me that "there should be no reason not to publish this work before Christmas."
[прим.: полнейшее пренебрежение интеллектом своих рабочих и сведение их к простым "операторам колб"]
"I ran hundreds of reactions between August and December 1977. Professor Oppolzer was unconvinced that the problem was chemistry and not the operator and made frequent comments about "the technique of present-day American postdocs".
"Living in a department where a senior colleague (Bruce Rickborn) insisted that he did not believe in orbitals, made it difficult to maintain my stance."
[и это в конце 70-х годов!]
"At that time, only rudimentary research facilities and limited access to chemicals were available to us and such conditions of deprivation invariably propel one to think harder, to innovate and improvise"
[ну да, конечно. То-то Украина такая инновационная страна, что аж дух захватывает. С импровизацией согласен: из говна и палок мы можем слепить условно работающую лабораторию. Думаю, наличие посильных препятствий действительно способно стимулировать рост, как у спортсменов, что приседают со штангой. Но чересчур большие проблемы будут непреодолимы и переломают человека (опять таки, как слишком тяжелая штанга для новичка).]
"In addition, the chemical total synthesis of taxol represents a formidable milestone in the art and craft of organic synthesis − perhaps even an end to an era of total synthesis."
"The history of alkaloid chemistry precedes even the synthesis of urea by Wohler in 1828. Morphine, one of the most famous alkaloids, was isolated by Serturner in 1806."
"The publication of this manuscript was not without problems. It was originally submitted to Tetrahedron Letters and was rejected on the basis of ""unimportance of reprinting NMR data". It was accepted in Synthetic Communications after the argument was made that the literature has been very vague with respect to accurate experimental and spectral details. When it appeared, I received a letter from a very well-known senior chemist, previously active in this area, who complained bitterly that allusions made in the paper to the lack of spectral details were unnecessary and insulting. Of course, this partucular author did not report either physical or spectral properties of supinidine in his publication, only an unrealistically high yield obtained in his synthesis. I pointed out that if orgnaic chemists performed their task properly there would have been no need for our publication."
"Neither of us thought we were that lucky - and in fact the first attempt to deprotect the tosyo amide gave a mixture. However, Demos had an NMR spectrum of morphine that he had aquired as authentic material - just in case we ever got to the end. Demos [the student] could see the distinctive patterns of protons on the rigid morphine pentacycle in the NMR of his mixture."
"...accidental discoveries are meritorious only upon careful observation and analysis of the «accidents»."
"In an age in which there is very severe competition in reaching heights of absurdity in remarks, that comes pretty near taking the blue ribbon" - Woodward.
"The benefits of total synthesis as a means of access to important materials may be questioned in terms of overall effectiveness; however, there is, unquestionably, no better way to train synthetic organic chemists than through a long and arduous total synthesis."
[Полностью согласен с этим утверждением, если по химиком-органиком понимать "работник у станка вытяжки"]
"... Woodward's second generation synthesis of reserpine intermediate, Wender's cedrene synthesis, Heathcock's lycopodine and daphnilactone designs, Majetich's perovskone cascade, and the Merck indinavir synthesis seem very close to the limits of creative design and perfect execution."
