ja9b05600_si_002.cif (2.63 MB)
Regiodivergent Photocyclization of Dearomatized Acylphloroglucinols: Asymmetric Syntheses of (−)-Nemorosone and (−)-6-epi-Garcimultiflorone A
dataset
posted on 2019-06-19, 00:00 authored by Saishuai Wen, Jonathan H. Boyce, Sunil K. Kandappa, Jayaraman Sivaguru, John A. PorcoRegiodivergent photocyclization of
dearomatized acylphloroglucinol
substrates has been developed to produce type A polycyclic polyprenylated
acylphloroglucinol (PPAP) derivatives using an excited-state intramolecular
proton transfer (ESIPT) process. Using this strategy, we achieved
the enantioselective total syntheses of the type A PPAPs (−)-nemorosone
and (−)-6-epi-garcimultiflorone A. Diverse
photocyclization substrates have been investigated leading to divergent
photocyclization processes as a function of tether length. Photophysical
studies were performed, and photocyclization mechanisms were proposed
based on investigation of various substrates as well as deuterium-labeling
experiments.
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deuterium-labeling experimentsESIPTexcited-state intramolecular proton transferAsymmetric SynthesesDiverse photocyclization substratestypephotocyclization processesDearomatized Acylphloroglucinolsdearomatized acylphloroglucinol substratesPPAPpolycyclic polyprenylated acylphloroglucinolRegiodivergent Photocyclizationphotocyclization mechanismsPhotophysical studiestether lengthRegiodivergent photocyclizationepi
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