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Discovery and Total
Synthesis of Seco-acorane Sesquiterpenoids from Chloranthus holostegius: Determination of Absolute
Configuration and Spontaneous Acetalization
Shihao Cheng (17879280)
Jie Wen (121424)
Houli Jiang (12897095)
Yuhang Zhou (1391788)
Yi Zhu (105054)
Danyang Zhang (5500367)
Lingyi Kong (536841)
Jun Luo (120285)
Biophysics
Biochemistry
Genetics
Neuroscience
Chemical Sciences not elsewhere classified
Ecology
Sociology
Biological Sciences not elsewhere classified
Inorganic Chemistry
relay heck reaction
flexible side chain
>- acorane sesquiterpenoids
spontaneous reversible acetalization
spontaneous acetalization shimianoids
intriguing spontaneous acetalization
total synthesis study
spontaneous acetalization products
chloranthus holostegius var
undetermined absolute configurations
3 </ sub
oh (< b
3 </ b
4 </ sub
total synthesis
chloranthus holostegius
acetalization products
absolute configurations
(< b
seco </
absolute configuration
>< sub
– c
tolylboronic acid
synthetic intermediate
synthesized via
mosher ’
methanol -<
ecd methods
bioactivity screening
aldehyde group
(±)- sulcatol
Shimianoids A–C, rare nor-acorane sesquiterpenoid
(<b>1</b>) and aromatic <i>seco</i>-acoranes (<b>2</b>/<b>3</b>) featuring an aldehyde group, along with
their spontaneous
acetalization products with methanol-<i>d</i><sub>4</sub> (<b>2a</b>/<b>3a</b>), were isolated and elucidated
from Chloranthus holostegius var. shimianensis. The undetermined absolute configurations
of the flexible side chain and intriguing spontaneous acetalization
of compounds <b>2</b>/<b>3</b> prompted our total synthesis
study. Ultimately, compounds <b>2</b>/<b>3</b> and their
acetalization products with methanol-<i>d</i><sub>4</sub> (<b>2a</b>/<b>3a</b>) and CH<sub>3</sub>OH (<b>2b</b>/<b>3b</b>) were synthesized via a redox-relay Heck reaction
of 4-tolylboronic acid with (±)-sulcatol, followed by oxidation
and acetalization. The absolute configurations of C7/10 at the flexible
side chain were determined by Mosher’s and ECD methods of the
synthetic intermediate, and the spontaneous reversible acetalization
was confirmed. Finally, a library of 26 aromatic <i>seco</i>-acorane sesquiterpenoids was constructed for bioactivity screening.
2026-10-01T00:00:00Z
Text
Journal contribution
10.1021/acs.joc.6c01558.s001
https://figshare.com/articles/journal_contribution/Discovery_and_Total_Synthesis_of_Seco-acorane_Sesquiterpenoids_from_Chloranthus_holostegius_Determination_of_Absolute_Configuration_and_Spontaneous_Acetalization/34045567
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