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H-Bonding Mediated Asymmetric Intramolecular Diels-Alder Reaction in the Formal Synthesis of (+)-Aplykurodinone-1

Title
H-Bonding Mediated Asymmetric Intramolecular Diels-Alder Reaction in the Formal Synthesis of (+)-Aplykurodinone-1
Author
조천규
Keywords
REGIOSELECTIVE SYNTHESIS; DEGRADED STEROLS; 3,5-DIBROMO-2-PYRONE; CYCLOADDITION; (+/-)-CRININE; OXIDATION
Issue Date
2018-11
Publisher
AMER CHEMICAL SOC
Citation
ORGANIC LETTERS, v. 20, no. 22, page. 7312-7316
Abstract
An asymmetric formal total synthesis of (+)-aplykurodinone-1 was achieved using a route, in which hydrogen bonding serves as a stereochemical control element governing the pi-facial selectivity of intramolecular Diels-Alder (IMDA) reaction of an enone tethered 2-pyrone. In the IMDA process, the configuration at a stereogenic, hydroxyl bearing an alpha-carbon in the enone dienophile is conveyed in a highly effective manner through intramolecular hydrogen bonding with the enone carbonyl oxygen. The tricyclic lactone, generated in this process, was successfully converted to a late stage intermediate in Danishefsky's synthesis of aplykurodinone-1.
URI
https://pubs.acs.org/doi/10.1021/acs.orglett.8b03250http://repository.hanyang.ac.kr/handle/20.500.11754/120632
ISSN
1523-7060; 1523-7052
DOI
10.1021/acs.orglett.8b03250
Appears in Collections:
COLLEGE OF NATURAL SCIENCES[S](자연과학대학) > CHEMISTRY(화학과) > Articles
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