期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 85, 期 6, 页码 4122-4129出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b03278
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资金
- SERB, New Delhi [EMR/2017/002298]
- CSIR
- UGC, New Delhi, India
A unified and concise first asymmetric total synthesis of (-)-citreoisocoumarin (2), (-)-citreoisocoumarinol (3), 12-epi-citreoisocoumarinol (4), and (-)-mucorisocoumarins A (5) and B (6) have been accomplished from the common intermediate (-)-6-O-methyl-citreoisocoumarin (1). Central to the synthetic approach is a regioselective gold(I)-catalyzed 6-endo-dig cyclization strategy for the construction of the isocoumarin skeleton. The other key steps in this approach included Sonogashira coupling, Tsuji-Wacker oxidation, Evans-Saksena's 1,3-anti-reduction, and Narasaka-Prasad's 1,3-syn-reduction. The synthetic results unambiguously confirmed the absolute configuration of the natural products mucorisocoumarins A and B as (-)-(10R,12S)-5 and (+)-(10S,12S)-6, respectively.
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