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J Am Chem Soc. 2002 Sep 4;124(35):10286-7.

Concomitant C-ring Expansion and D-ring formation in lanosterol biosynthesis from squalene without violation of Markovnikov's rule.

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Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37235, USA.


A mechanism is proposed for the formation of the C and D rings of lanosterol from squalene on the basis of density functional calculations of a model cyclopentylcarbinyl carbocation. The mechanism involves the ring expansion of the cyclopentylcarbinyl carbocation to the six-membered ring C in concert with the formation of the D ring. The mechanism does not involve a violation of Markovnikov's rule as the earlier proposed mechanism does for the formation of rings C and D.

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