Intramolecular Diels–Alder
Approaches to the
Decalin Core of Verongidolide: The Origin of the exo-Selectivity, a DFT Analysis
Version 2 2018-07-18, 18:19
Version 1 2018-05-16, 19:44
Posted on 2018-07-18 - 18:19
Verongidolide is a natural macrolactone
recently isolated from
a New Caledonia sponge, Verongidolae. The structure
of this natural product is similar to the structure of superstolides,
also isolated from a New Caledonian sponge, Neosiphonia superstes. From a biological point of view, verongidolide and superstolides
A and B present potent cytotoxicity against human oral carcinoma KB
(0.3 nM). By comparing the 1H NMR chemical shifts as well
as the coupling constants, we conclude that verongidolide possesses
a cis-decalin core and we hypothesize that the relative
configuration of the cis-decalin core is similar
to the one of superstolide A. To verify this hypothesis, intramolecular
and transannular Diels–Alder reactions were attempted to construct
the decalin core. Unexpectedly, the selectivity of the Diels–Alder
reactions was exo and an in-depth DFT calculation
of the key reaction mechanism was achieved in order to understand
the factors controlling this unexpected selectivity.
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Maiga-Wandiam, Baba; Corbu, Andrei; Massiot, Georges; Sautel, François; Yu, Peiyuan; Lin, Bernice Wan-Yi; et al. (2018). Intramolecular Diels–Alder
Approaches to the
Decalin Core of Verongidolide: The Origin of the exo-Selectivity, a DFT Analysis. ACS Publications. Collection. https://doi.org/10.1021/acs.joc.8b00566
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AUTHORS (8)
BM
Baba Maiga-Wandiam
AC
Andrei Corbu
GM
Georges Massiot
FS
François Sautel
PY
Peiyuan Yu
BL
Bernice Wan-Yi Lin
KH
Kendall N. Houk
JC
Janine Cossy