Comments on: Tricholomalides A & B

By: Ye Tao

Ye Tao — Wed, 09 Dec 2009 16:47:59 +0000

Typo: coefficients before alcohol and aldehyde should be 1.

R-CH2-O-H + –cat NaH–> R-CHO + H2(g)

By: Ye Tao

Ye Tao — Wed, 09 Dec 2009 16:42:24 +0000

I am responding to Liquidcarbon’s concern that there is no oxidant in the reaction.

If one examines the balanced reaction carefully, one notices that the hydroxyl and alpha proton on the alcohol serve as the oxidant.

equation: 2 R-CH2-O-H + –cat NaH–> 2 R-CHO + H2

Oxidation states: LHS: C=-2; O=-2, H=1; RHS: C=0; O=-2, H in H2 = 0.

NaH is catalytic in the above reaction. Carbon gets oxidized and the hydrogen atoms get reduced. The reaction, while most likely unfavorable thermodynamically, is irreversibly driven by entropy increase from gas evolution.

By: Instant peer review by web 2.0 «

Instant peer review by web 2.0 « — Mon, 27 Jul 2009 18:47:06 +0000

[...] what?“, you are in good company. Not long after publication several readers smelled a rat and hi-jacked a comments thread at totally synthetic to discuss the strange [...]

By: PC

PC — Thu, 23 Jul 2009 01:14:11 +0000

oops…. let’s correct it

it IS annoying to see empty comment like this…

don’t ya agree?

By: Old Timer

Old Timer — Wed, 22 Jul 2009 23:49:03 +0000

It’s more annoying to read grammatically incorrect comments with typos.

By: PC

PC — Wed, 22 Jul 2009 21:19:50 +0000

it it annoying to see empty comment like this…

By: Old Timer

Old Timer — Wed, 22 Jul 2009 19:47:38 +0000

Although this is a fantastic synthesis, I can’t help but notice it is really more than that. This paper is an example of truly outstanding scientific inquiry that results in the revision of several structures, with a versatile route to each. Definitely a top paper of 2009!

By: wackadoo

wackadoo — Wed, 22 Jul 2009 18:03:29 +0000

you guys should look up LADH (liver alcohol dehydrogenase), hydride transfer back to the sodium makes fine sense… just not your normal orgo stuff….

By: Tex

Tex — Wed, 22 Jul 2009 15:32:28 +0000

Perhaps I am mistaken, but don’t you add a degree of unsaturation to the molecule – so it’s a net oxidation?

By: Old Timer

Old Timer — Wed, 22 Jul 2009 12:52:17 +0000

Yes it is. This is the David Zhigang Wang who worked with Tom Katz (the should-have-been Nobel Laureate) for his Ph.D. and postdoc with Danishefsky – which I guess is the reason why it’s being discussed here