Re: When were Buckyballs "invented"

From: Steve Turner (spam_at_spam.net)
Date: 06/27/04 

Date: Sun, 27 Jun 2004 14:46:40 GMT

On 27 Jun 2004 04:57:47 -0700, dgenglish@hotmail.com (dave e) wrote:

>Steve Turner <spam@spam.net> wrote in message news:<ehdsd0181b78rl3jk24cbv9k1v8vgk2ktq@4ax.com>...
>> On Sat, 26 Jun 2004 11:52:28 +0100, Dirk Bruere at Neopax
>> <dirk@neopax.com> wrote:
>>
>> >And the thing that nobody seems to have expected is how easy it is to make.
>>
>> Unfortunately, though, the current preparations are not rational
>> syntheses but purest of luck driven by thermodynamic stability. It's
>> really more like mining soot than synthesizing. Chapman et al had
>> been interested in constructing the molecule in a logical fashion
>> according to standard methods of organic synthesis.
>>
>> Steve Turner
>
>This represents a lack of pragmatism among some organic chemists,
>though.
>
>I remember attending a seminar several years back in which a chemist
>was describing his work on the rational, stereospecific synthesis of
>sucrose. As an undergraduate, I was awed by the complex multistep
>synthesis he had designed to produce some pitiful yield of the sugar.
>My academic mentor, on the other hand, was unimpressed. On the way
>out of the seminar my mentor scoffed, "Why would anyone want to do
>that- sucrose is already one of the least expensive stereospecific
>chemicals available"

All true, but also true of many of the complex natural product
syntheses which represent the crowning achievements of the art and
science. Monensin is so cheap that it's used as a livestock feed
additive, but the stereospecific synthesis requires something like 60
steps. So why do it? There are a lot of reasons, but one of the
strongest is that a rational synthesis will allow structural
modifications that nature does not produce. In fact, the enantiomer
of monensin is a compound foreign to nature, but as easily synthesized
as the natural antipode. These unnatural relatives of complex natural
products can turn out to have immense value, e.g. as pharmaceuticals.

There is also the value of demonstrating new synthetic methodology as
well as the "because it's there" type of motivation. In the case of
sucrose I imagine the last reason is the most relevant.

I suspect you [dave e] already know all this; I'm just throwing it out
for discussion or for the benefit of others...

Steve Turner