Pigments of Fungi. Part 70.* Total Synthesis of (R)-Semixanthomegnin and the X-Ray Crystal Structure of (±)-7-Chloro-10-methoxy-3-methyl-3, 4-dihydro-1 H-naphtho[2,3-c]pyran-1,6,9-trione
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(R)-Semixanthomegnin (8), which has been converted by others to the mould metabolite (3R,3′ R)-xanthomegnin (9), is prepared in seven steps from (R)-propylene oxide (16). A single-crystal X-ray structure analysis of (±)-7-chloro-10-methoxy-3-methyl-3,4-dihydro-1H-naphtho[2,3-c]pyran-1,6,9-trione (25) confirms the regiochemistry of the cycloaddition reaction between 2,5-dichloro-1,4-benzoquinone and the new, highly oxygenated, chiral butadiene derivative (2).
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2011 ◽
Vol 13
(4)
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pp. 684-690
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1998 ◽
Vol 52
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pp. 702-708
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1970 ◽
Vol 3
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pp. 97-98
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2005 ◽
Vol 60
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pp. 569-571
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1993 ◽
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pp. 961-964
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1992 ◽
Vol 200
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2014 ◽
Vol 70
(a1)
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pp. C195-C195