Secondary Carbocations in the Biosynthesis of Pupukeanane Sesquiterpenes

The results of quantum chemical calculations on putative biosynthetic carbocation cyclization/rearrangements leading to pupukeanane and related sesquiterpenes indicate that a secondary carbocation proposed as an intermediate is not a minimum on the potential energy surface and instead resides in a r...

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Bibliographic Details
Published in:The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment, & general theory Molecules, spectroscopy, kinetics, environment, & general theory, 2018-10, Vol.122 (40), p.8058-8061
Main Authors: McCulley, Christina H, Tantillo, Dean J
Format: Article
Language:English
Subjects:
Cations - chemistry
Cyclization
Models, Chemical
Molecular Structure
Quantum Theory
Sesquiterpenes - chemistry
Thermodynamics
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Summary:The results of quantum chemical calculations on putative biosynthetic carbocation cyclization/rearrangements leading to pupukeanane and related sesquiterpenes indicate that a secondary carbocation proposed as an intermediate is not a minimum on the potential energy surface and instead resides in a region of the potential energy surface associated with a plateau containing multiple exit channels.
ISSN:1089-5639
1520-5215
DOI:10.1021/acs.jpca.8b07961