H-Bonding Mediated Asymmetric Intramolecular Diels-Alder Reaction in the Formal Synthesis of (+)-Aplykurodinone-1
- Authors
- Lee, Joon-Ho; Cho, Cheon-Gyu
- Issue Date
- Nov-2018
- Publisher
- AMER CHEMICAL SOC
- Citation
- ORGANIC LETTERS, v.20, no.22, pp.7312 - 7316
- Indexed
- SCIE
SCOPUS
- Journal Title
- ORGANIC LETTERS
- Volume
- 20
- Number
- 22
- Start Page
- 7312
- End Page
- 7316
- URI
- https://scholarworks.bwise.kr/hanyang/handle/2021.sw.hanyang/149088
- DOI
- 10.1021/acs.orglett.8b03250
- ISSN
- 1523-7060
- 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.
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