Structure Revision of an Acorane Sesquiterpene Cordycepol A

Org Lett. 2016 Oct 7;18(19):4860-4863. doi: 10.1021/acs.orglett.6b02341. Epub 2016 Sep 9.

Abstract

Structure revision of a recently reported spirodecane sesquiterpene, cordycepol A, from fungi Cordyceps ophioglossoides was enabled by fast and accurate calculations of nuclear spin-spin coupling constants (SSCCs) with a relativistic force field (DU8c) parametric method. Two other reported cordycepols, B and C, are also identified as misassigned. Calculations of accurate SSCCs, which contain a wealth of structural information, offer a chemically intuitive tool for structure elucidation, rendering the whole structure revision process more guided and intentional, while augmenting in a synergistic way the calculations of chemical shifts.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.