Journal
ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 11, Issue 2, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.202100721
Keywords
Fries rearrangement; photo-Nazarov cyclization; taiwaniaquinoids; tandem reaction; total synthesis
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Funding
- Ministry of Science and Technology in Taiwan [MOST109-2636-M-009-003, MOST110-2113-M-A49-001-MY2]
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A concise route to (+/-)-taiwaniaquinol B is described, in which the 6-5-6-fused ring system is constructed by sequencing a Fries rearrangement and a photo-Nazarov cyclization. The use of photoirradiation conditions is found to be crucial for promoting the key electrocyclization and mitigating the competing oxo-Michael pathway.
Described is a concise route to (+/-)-taiwaniaquinol B. The 6-5-6-fused ring system was constructed by sequencing a Fries rearrangement and a photo-Nazarov cyclization. The application of photoirradiation conditions was found to be crucial for promoting the key electrocyclization and mitigating the competing oxo-Michael pathway.
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