Journal
ORGANIC LETTERS
Volume 24, Issue 17, Pages 3297-3301Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c01215
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Funding
- JSPS KAKENHI [21K19051, JP18H04416, JP19H02851]
- Adaptable and Seamless Technology transfer Program through Target-driven R&D (A-STEP) from Japan Science and Technology Agency (JST) [JPMJTR214D]
- Nagase Science Technology Foundation
- Tokushima University [1802001]
- Grants-in-Aid for Scientific Research [21K19051] Funding Source: KAKEN
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The total syntheses of two natural products, 4,10-dihydroxy-8,12-guaianolides, were achieved. The construction of the typical 5,7-fused system of 8,12-guaianolides using a ring expansion reaction revealed that the previously reported structures of both natural products were incorrect.
Thefirst total syntheses of two 4,10-dihydroxy-8,12-guaianolides that were reported to be natural products wereachieved. Toward the syntheses of a collection of relatedguaianolides, the typical 5,7-fused system of 8,12-guaianolideswas constructed by a ring expansion reaction of a hydroxylatedcoronafacic acid analogue that can be practically synthesized andoptically resolved. The total syntheses of these compoundsrevealed that the previously reported structures of both natural products were incorrect.
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